WO2002066411A2 - Polyhalogensubstituierte zimtsäuren und zimtsäurederivate und ein verfahren zu deren herstellung - Google Patents
Polyhalogensubstituierte zimtsäuren und zimtsäurederivate und ein verfahren zu deren herstellung Download PDFInfo
- Publication number
- WO2002066411A2 WO2002066411A2 PCT/EP2002/001462 EP0201462W WO02066411A2 WO 2002066411 A2 WO2002066411 A2 WO 2002066411A2 EP 0201462 W EP0201462 W EP 0201462W WO 02066411 A2 WO02066411 A2 WO 02066411A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- chlorine
- hydrogen
- cinnamic
- acid
- Prior art date
Links
- 0 CCOc1c(C(C(*)C2)C=O)c2c(*)c(*)c1O Chemical compound CCOc1c(C(C(*)C2)C=O)c2c(*)c(*)c1O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Definitions
- the present invention relates to new polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the production of known and new polyhalogen-substituted cinnamic acids and cinnamic acid derivatives.
- Known halogen-substituted cinnamic acids and cinnamic acid derivatives are intermediates for the production of agrochemicals and pharmaceuticals (see DE-A 22 44 761, WO 95/30645, WO 94/26692, WO 94/7893, WO 94/26693 and US-A 5 753 655).
- A OH or O-alkyl.
- Another way of producing a halogen-substituted cinnamic acid derivative is based on 2,4-difluorobromobenzene and this with acrylic acid
- EP-A-584264 describes a process similar to that of EP-A-584 043. However, the process is carried out in the additional presence of arylphosphines, which is associated with further costs and additional effort.
- R 1 , R 2 , R 3 and R 4 are the same or different and each represents hydrogen, fluorine, chlorine or bromine, at least two of these radicals being different from hydrogen and
- X represents OR 5 or N (R 6 ) (R 7 ), where
- R 5 represents hydrogen, optionally substituted Ci-C j o-alkyl, optionally substituted phenyl or benzyl and
- R 6 and R 7 are the same or different and each represents optionally substituted C j -C Q alkyl and
- R 8 represents hydrogen, chlorine, bromine or optionally substituted C 1 -C 4 -alkyl
- R 1 , R 2 , R 3 and R 4 have the meaning given for formula (III) and
- a ⁇ stands for one equivalent of halide, hydrogen sulfate, nitrate, acetate or tetrafluoroborate ions or for V% equivalent of sulfate ions or for 3 equivalent of phosphate ions,
- R 8 represents hydrogen, chlorine, bromine or optionally substituted -CC-alkyl
- the method according to the invention is very particularly preferably carried out without the addition of a base.
- 0.5 mol or less, preferably 0.1 mol or less and particularly preferably 0.05 mol of base per mol of diazonium salt of the formula (IV) can be used.
- the process according to the invention is advantageously and very particularly preferably carried out without the addition of arylphosphines.
- arylphosphines In general, 4 mol or less, preferably 1 mol or less and particularly preferably 0.1 mol or less arylphosphines can be used per mol of palladium.
- radicals R 5 , R 6 , R 7 and R 8 are optionally substituted alkyl radicals
- substituents such as halogen, hydroxyl or Cg-C 2 aryl radicals can be used. Of these substituents, 1 to 2 can be present, for example, per radical from the group R 5 , R 6 , R 7 and R 8 .
- R 1 is preferably hydrogen or chlorine
- R 2 is hydrogen, fluorine, chlorine or bromine
- R 3 is hydrogen or chlorine
- R 4 is fluorine or chlorine, at least one of the radicals R 1 , R 2 and R 3 being different from hydrogen is.
- R 5 preferably represents hydrogen, methyl, ethyl, isopropyl or benzyl.
- R 7 preferably represents methyl or ethyl.
- R 8 preferably represents hydrogen or methyl.
- A® preferably represents one equivalent of chloride, hydrogen sulfate or acetate or 1/2 equivalent of sulfate.
- homogeneous, palladium-containing catalysts examples include Palladium (II) - and
- Palladium (O) compounds in question such as PdCl 2 , PdBr 2 , Pd (NO 3 ) 2 , H 2 PdCl 4 , Pd (CH 3 COO) 2 , Na 2 PdCl 4 , K 2 PdCl 4 , Pd (II) - acetylacetonate, tetra (triphenylphosphine) Pd and tris (dibenzylidene acetone) Pd 2 in question.
- PdCl 2 , Pd (CH 3 COO) 2 and Pd (II) acetylacetonate are preferred.
- the respective palladium-containing catalyst can be used, for example, in an amount of 0.001 to 10 mol%, preferably on the diazonium salt of the formula (IN).
- Preferred reaction temperatures are those from +20 to + 80 ° C, especially those from +40 to + 65 ° C.
- Suitable simple solvents are, for example, water, alcohols such as e.g. Ci-Cö-alkyl alcohols, carboxylic acids such as e.g. Formic acid, ethers such as e.g. Tetrahydrofuran and nitriles, e.g. Acetonitrile.
- the diazonium salts of the formula (IV) can be prepared in a manner known per se (see, for example, Houben-Weyl, volume X / 3, pages 7 to 113) from the corresponding anilines by reaction with sodium nitrite in an acidic aqueous solution or by reaction of methyl nitrite in acidic methanol
- the diazonium salts can be in
- Form of the reaction mixture obtained in their preparation can be used in the process according to the invention, preferably after the destruction of any nitrite which may still be present. Isolation of the diazonium salts is not necessary.
- Preferred compounds of the formula (V) are acrylic acid, methacrylic acid, acrylamide and methacrylamide.
- the process according to the invention can be carried out, for example, by first starting from an aniline of the formula in the
- R 1 , R 2 , R 3 and R 4 have the meaning given for formula (III),
- nitrite in sulfuric acid aqueous solution or with an alkyl nitrite such as methyl, ethyl, butyl or amyl nitrite, preferably methyl nitrite in acid, e.g.
- any nitrite present in the reaction mixture obtained was destroyed by adding amidosulfonic acid, the reaction mixture thus treated to a mixture of acrylic acid or an acrylic acid derivative of the formula (V) with a homogeneous, palladium-containing catalyst and optionally a simple solvent such as water, methanol, ethanol or isopropanol is added dropwise at the reaction temperature and, if appropriate after a subsequent stirring time, the product of the formula (III) is removed, if appropriate after cooling and / or dilution with water, for example by filtration, distillation or phase separation.
- a simple solvent such as water, methanol, ethanol or isopropanol
- the process according to the invention has the advantages that it is simple, at low temperatures, in short reaction times, without large amounts and preferably without base additions without large amounts and preferably without absolutely necessary
- the present invention further relates to new polyhalogenated cinnamic acids and
- polyhalogenated cinnamic acids and cinnamic acid derivatives of the formula (III) including those of the formula (IIP) can be obtained by hydrogenation of the double bond (step 1) and subsequent cyclization (step 2) in indanone derivatives of the formula
- R 1 to R 4 have the meaning given for formula (III) and
- R 8 is hydrogen, bromine, chlorine or optionally substituted C ⁇ Q Ci -alkyl, are converted.
- Compounds of the general formula (VIIa) in which R 8 represents hydrogen can be converted in a manner known per se by halogenation into the corresponding compounds of the general formula (VIIa) in which R 8 represents bromine or chlorine.
- Ner compounds of the general formula (VIIa) in which R 8 is bromine or chlorine can be converted in a manner known per se, for example by palladium-catalyzed carbonylation reactions with carbon monoxide and a suitable nucleophile, into indanone derivatives of the formula (VIIIb),
- R 1 to R 4 have the meaning given for formula (III) and
- R 9 represents COOH, CO ⁇ H 2 or COOR 10 , where
- R 10 is C r C 4 alkyl.
- the new compounds of the formula (IIP) broaden the range of available indanones and thus potential active ingredients in the agricultural and pharmaceutical fields and in the field of liquid-crystalline substances.
- Gaseous methyl nitrite was prepared from 35 g of sodium nitrite in a methanol (20 ml) / water (60 ml) mixture by adding 30 ml of 50% sulfuric acid (30 ml), which at 0 ° C. was mixed into a mixture of 250 ml of water, 60 ml conc. Sulfuric acid and 53.5 g of 2,4-dichloroaniline was introduced. The mixture was stirred for 1 hour. Excess methyl nitrite was removed by passing a stream of nitrogen and adding 3 g of amidosulfonic acid.
- Example 5 The procedure was as in Example 5, but the 2,4-difluorocinnamic acid obtained was not isolated.
- the aqueous-acidic product suspension obtained was made alkaline with sodium hydroxide solution and, with further stirring at 50 ° C., 2 g of Pd / C (5% strength) were added and the mixture was heated to 100 ° C. Hydrogen was then injected up to 5 bar.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02712904A EP1362025A2 (de) | 2001-02-16 | 2002-02-13 | Polyhalogensubstituierte zimtsaeuren und zimtsaeurederivate und ein verfahren zu deren herstellung |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2001107151 DE10107151A1 (de) | 2001-02-16 | 2001-02-16 | Polyhalogensubstituierte Zimtsäuren und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten |
DE10107151.5 | 2001-02-16 | ||
DE10115405.4 | 2001-03-29 | ||
DE2001115405 DE10115405A1 (de) | 2001-03-29 | 2001-03-29 | Polyhalogensubstituierte Zimtsäuren und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten |
DE2001152789 DE10152789A1 (de) | 2001-10-25 | 2001-10-25 | Polyhalogensubstituierte Zimtsäure und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten |
DE10152789.6 | 2001-10-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002066411A2 true WO2002066411A2 (de) | 2002-08-29 |
WO2002066411A3 WO2002066411A3 (de) | 2002-11-21 |
Family
ID=27214295
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/001462 WO2002066411A2 (de) | 2001-02-16 | 2002-02-13 | Polyhalogensubstituierte zimtsäuren und zimtsäurederivate und ein verfahren zu deren herstellung |
Country Status (4)
Country | Link |
---|---|
US (3) | US6956129B2 (de) |
EP (1) | EP1362025A2 (de) |
CN (1) | CN1246280C (de) |
WO (1) | WO2002066411A2 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6956129B2 (en) * | 2001-02-16 | 2005-10-18 | Bayer Aktiengesellschaft | Polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the preparation of polyhalogen-substituted cinnamic acids and cinnamic acid derivatives |
WO2007133294A2 (en) * | 2005-12-30 | 2007-11-22 | Bmo Llc | Ubiquitous navbar user interface across multiple heterogeneous digital media devices |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5708033A (en) * | 1994-05-10 | 1998-01-13 | Glaxo Wellcome Inc. | Amide derivatives and their therapeutic use |
WO2000008023A1 (en) * | 1998-08-05 | 2000-02-17 | Smithkline Beecham Plc | Condensed tricyclic piperidines having anti-convulsant activity |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE349768B (de) * | 1963-06-28 | 1972-10-09 | Kockums Ind Ab | |
DE2244761A1 (de) | 1972-09-09 | 1974-03-14 | Schering Ag | Indan- und tetralinderivate |
DE59008501D1 (de) | 1989-06-01 | 1995-03-30 | Ciba Geigy Ag | Neue, stickstoffhaltige Titanocene und deren Verwendung. |
US4979982A (en) * | 1990-02-02 | 1990-12-25 | Uniroyal Chemical Company, Inc. | Herbicidal cinnamic ester uracils |
US6066501A (en) | 1991-05-16 | 2000-05-23 | Cold Spring Harbor Laboratory | D-type cyclin and uses related thereto |
US6156876A (en) | 1991-05-16 | 2000-12-05 | Cold Spring Harbor Laboratory | D-type cyclin and uses related thereto |
US5998582A (en) | 1991-05-16 | 1999-12-07 | Cold Spring Harbor Laboratory | D-type cyclins and uses related thereto |
US5889169A (en) | 1991-05-16 | 1999-03-30 | Cold Spring Harbor Laboratory | Cell cycle regulatory protein p16 gene |
IL112819A (en) | 1991-10-16 | 2001-11-25 | Teva Pharma | Fluorinated 1-aminoindan compounds and a process for their preparation |
US5508402A (en) | 1992-08-18 | 1996-04-16 | Ciba-Geigy Corporation | Process for the preparation of N,N'-substituted ureas |
FR2696466B1 (fr) | 1992-10-02 | 1994-11-25 | Rhone Poulenc Rorer Sa | Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant. |
JP3430548B2 (ja) | 1993-03-10 | 2003-07-28 | 旭硝子株式会社 | 含フッ素インダン環誘導体化合物およびそれを含有する液晶組成物 |
GB9309621D0 (en) | 1993-05-11 | 1993-06-23 | Wellcome Found | Amide derivatives and their therapeutic use |
AU687547B2 (en) | 1994-04-20 | 1998-02-26 | E.I. Du Pont De Nemours And Company | Preparation of arthropodicidal oxadiazines |
CN101007763B (zh) | 1994-04-20 | 2012-10-10 | 纳幕尔杜邦公司 | 用于制备噁二嗪的中间体 |
US5972118A (en) * | 1995-10-27 | 1999-10-26 | Tennessee Valley Authority | Concentrated sulfuric acid hydrolysis of lignocellulosics |
US5753655A (en) | 1996-10-10 | 1998-05-19 | Ortho Pharmaceutical Corporation | 1-arylsulphonyl, arylcarbonyl and arylthiocarbonyl pyridazino derivatives and methods of preparation |
US5677308A (en) * | 1996-12-19 | 1997-10-14 | Lerner; A. Martin | Method for alleviating spasmodic torticollis |
GB9816984D0 (en) * | 1998-08-05 | 1998-09-30 | Smithkline Beecham Plc | Novel compounds |
US6956129B2 (en) * | 2001-02-16 | 2005-10-18 | Bayer Aktiengesellschaft | Polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the preparation of polyhalogen-substituted cinnamic acids and cinnamic acid derivatives |
-
2002
- 2002-02-12 US US10/074,180 patent/US6956129B2/en not_active Expired - Fee Related
- 2002-02-13 WO PCT/EP2002/001462 patent/WO2002066411A2/de active Search and Examination
- 2002-02-13 EP EP02712904A patent/EP1362025A2/de not_active Withdrawn
- 2002-02-13 CN CNB028050606A patent/CN1246280C/zh not_active Expired - Fee Related
-
2005
- 2005-06-10 US US11/150,721 patent/US7381832B2/en not_active Expired - Fee Related
-
2008
- 2008-04-22 US US12/148,752 patent/US20080200731A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5708033A (en) * | 1994-05-10 | 1998-01-13 | Glaxo Wellcome Inc. | Amide derivatives and their therapeutic use |
WO2000008023A1 (en) * | 1998-08-05 | 2000-02-17 | Smithkline Beecham Plc | Condensed tricyclic piperidines having anti-convulsant activity |
Non-Patent Citations (7)
Title |
---|
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 1041035 XP002207217 & BERRIER, C ET AL: TETRAHEDRON., Bd. 40, Nr. 23, 1984, Seiten 4973-4980, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL ISSN: 0040-4020 * |
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 1053433 XP002207218 & SIMCHEN, G ET AL: JOURNAL OF MEDICINAL CHEMISTRY., Bd. 15, 1972, Seiten 341-344, AMERICAN CHEMICAL SOCIETY., US ISSN: 0022-2623 * |
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 3474443 XP002207216 & KRUSE, L I ET AL: JOURNAL OF MEDICINAL CHEMISTRY., Bd. 30, Nr. 3, 1987, Seiten 486-494, AMERICAN CHEMICAL SOCIETY., US ISSN: 0022-2623 * |
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 665237 XP002207219 & HUSSEY, H : JOURNAL OF ORGANIC CHEMISTRY., Bd. 24, 1959, Seite 843 AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US ISSN: 0022-3263 * |
KIKUKAWA K ET AL: "PALLADIUM(0)-CATALYZED ARYLATION OF OLEFINS BY ARYLAMINES AND AN ALKYL NITRITE" JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, Bd. 46, 1981, Seiten 4885-4888, XP000882385 ISSN: 0022-3263 * |
SENGUPTA S ET AL: "Heck reaction of arenediazonium salts: a palladium- catalysed reaction in an aqueous medium" JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, Nr. 17, 7. September 1993 (1993-09-07), Seiten 1943-1944, XP002128192 ISSN: 1472-7781 * |
WATERLOT C ET AL: "Montmorillonite-palladium-copper catalyzed cross-coupling of methyl acrylate with aryl amines" TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, Bd. 41, Nr. 3, Januar 2000 (2000-01), Seiten 317-319, XP004186256 ISSN: 0040-4039 * |
Also Published As
Publication number | Publication date |
---|---|
US6956129B2 (en) | 2005-10-18 |
US7381832B2 (en) | 2008-06-03 |
US20020115885A1 (en) | 2002-08-22 |
CN1246280C (zh) | 2006-03-22 |
US20050234264A1 (en) | 2005-10-20 |
EP1362025A2 (de) | 2003-11-19 |
US20080200731A1 (en) | 2008-08-21 |
CN1491201A (zh) | 2004-04-21 |
WO2002066411A3 (de) | 2002-11-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DD141422A5 (de) | Verfahren zur herstellung von phenylessigsaeure-derivaten | |
DE2314636C2 (de) | Indanderivate, deren Herstellung und diese enthaltende pharmazeutische Mittel | |
EP0380712B1 (de) | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten | |
EP0001980B1 (de) | Verfahren zur Herstellung von Halogenvinyl-gamma-butyrolactonen, sowie Zwischenprodukte und ihre Herstellung | |
EP2321241B1 (de) | Verfahren zur herstellung von phenylalkan-1-olen | |
DE60109829T2 (de) | 3-(1-Hydroxy-pentylidene)-5-nitro-3H-benzofuran-2-on, ein Verfahren zu seiner Herstellung und seine Verwendung | |
DE2057840C3 (de) | Verfahren zur Herstellung von Indolderivaten | |
WO2002066411A2 (de) | Polyhalogensubstituierte zimtsäuren und zimtsäurederivate und ein verfahren zu deren herstellung | |
DE2004038C3 (de) | 5-Cyclohexyl-1-indancarbonsäuren,,deren Niedrigalkyl- und tert.-Aminoniedrigalkylester, nicht-toxische pharmakologisch verträgliche Salze und Verfahren zu deren Herstellung | |
DE2404158B2 (de) | Verfahren zur Herstellung eines 2-(4-Alkylphenyl)-propion-aldehyds | |
EP1223158B1 (de) | Verfahren zur Herstellung trifluormethyl-substituierter Biphenylcarbonsäuren und neue trichlormethyl- und trifluormethyl-substituierte Biphenylcarbonitrile | |
EP0173201B1 (de) | Verfahren zur Herstellung aromatischer Bromverbindungen | |
DE10152789A1 (de) | Polyhalogensubstituierte Zimtsäure und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten | |
EP0923534B1 (de) | Verfahren zur herstellung von racemischen phenethylaminen | |
DE10115405A1 (de) | Polyhalogensubstituierte Zimtsäuren und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten | |
EP0154122B1 (de) | Verfahren zur selektiven Hydrierung von Chlor enthaltenden Pyrimidinen und neue Pyrimidine | |
DE10107151A1 (de) | Polyhalogensubstituierte Zimtsäuren und Zimtsäurederivate und ein Verfahren zur Herstellung von polyhalogensubstituierten Zimtsäuren und Zimtsäurederivaten | |
DE3529259A1 (de) | Verfahren zur herstellung von halogensubstituierten benzoylacetonitrilen, 1-chlor-2-(2,4-dichlor-5-fluorphenyl)-ethan-2-on und seine herstellung | |
DE2164662A1 (de) | Indanderivate und Verfahren zu ihrer Herstellung | |
EP1268400B1 (de) | Verfahren zur herstellung von n-butyryl-4-amino-3-methyl-benzoesäuremethylester und die neue verbindung n-(4-brom-2-methylphenyl)-butanamid | |
EP0394644A2 (de) | Halogenbenzolderivate | |
DE2625163A1 (de) | Alpha-chlorcarbonsaeuren und verfahren zu ihrer herstellung | |
EP0649831B1 (de) | Verfahren zur Herstellung von 3-(p-Fluorphenyl)-2-methylpropionsäure und 3-(p-Fluorphenyl)-2-methylpropionsäurederivaten | |
EP0587533B1 (de) | Verfahren zur Herstellung von alpha-Aminoketonsalzen | |
DE2023977A1 (de) | Verfahren zur Herstellung von Benzylpyn midinen und Zwischenprodukten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
AK | Designated states |
Kind code of ref document: A3 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A3 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002712904 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 741/MUMNP/2003 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 028050606 Country of ref document: CN |
|
WWP | Wipo information: published in national office |
Ref document number: 2002712904 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
NENP | Non-entry into the national phase |
Ref country code: JP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: JP |
|
DPE2 | Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101) |