DE10215907A1 - Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung - Google Patents
Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren VerwendungInfo
- Publication number
- DE10215907A1 DE10215907A1 DE10215907A DE10215907A DE10215907A1 DE 10215907 A1 DE10215907 A1 DE 10215907A1 DE 10215907 A DE10215907 A DE 10215907A DE 10215907 A DE10215907 A DE 10215907A DE 10215907 A1 DE10215907 A1 DE 10215907A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- cycloalkyl
- alkynyl
- alkenyl
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10215907A DE10215907A1 (de) | 2002-04-11 | 2002-04-11 | Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
| IL16424902A IL164249A0 (en) | 2002-04-11 | 2002-04-11 | Acyl-3-carboxphenylurea derivatives, processes forpreparing them and their use |
| RU2004133045/04A RU2004133045A (ru) | 2002-04-11 | 2003-03-28 | Производные ацил-4-карбоксифенилмочевины, способ их получения и их применение |
| KR10-2004-7016158A KR20040097333A (ko) | 2002-04-11 | 2003-03-28 | 아실-4-카복시페닐우레아 유도체, 이의 제조방법 및 용도 |
| HU0500440A HUP0500440A2 (hu) | 2002-04-11 | 2003-03-28 | Acil-4-karboxi-fenil-karbamid-származékok, azokat tartalmazó gyógyszerkészítmények, eljárás ezek előállítására és ezek alkalmazása |
| AT03712111T ATE476412T1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
| JP2003582121A JP4328211B2 (ja) | 2002-04-11 | 2003-03-28 | アシル−４−カルボキシフェニル尿素誘導体、その製造方法およびその使用 |
| CNB038081873A CN1286805C (zh) | 2002-04-11 | 2003-03-28 | 酰基－4－羧基苯基脲衍生物、其制备方法及用途 |
| PL03371279A PL371279A1 (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenylurea derivatives, method for production and use thereof |
| MXPA04009468A MXPA04009468A (es) | 2002-04-11 | 2003-03-28 | Derivados de acil-4-carboxifenilurea, procedimientos para su preparacion y su uso. |
| OA1200400276A OA12805A (fr) | 2002-04-11 | 2003-03-28 | Dérivés d'acyl-4-carboxyphényluré¦, procédés pour les préparer et leur utilisation. |
| HR20040930A HRPK20040930B3 (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenylurea derivatives, method for production and use thereof |
| PCT/EP2003/003251 WO2003084922A1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
| BR0309242-9A BR0309242A (pt) | 2002-04-11 | 2003-03-28 | Derivados de acil-4-carboxifenil-uréia, processo para a sua preparação e sua aplicação |
| UA20041109224A UA78040C2 (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenyl urea derivatives, a process for preparation thereof (variants), a medicament based thereon and a process for preparation thereof |
| DE50312949T DE50312949D1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
| AU2003216900A AU2003216900A1 (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenylurea derivatives, method for production and use thereof |
| EP03712111A EP1497262B1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
| NZ535834A NZ535834A (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
| CA002481817A CA2481817A1 (en) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxyphenylurea derivatives, method for production and use thereof |
| PE2003000349A PE20040374A1 (es) | 2002-04-11 | 2003-04-07 | DERIVADOS DE ACIL-4-CARBOXIFENILUREA COMO INHIBIDORES DE LA GLUCOGENO FOSFORILASA a |
| TW092108057A TW200404762A (en) | 2002-04-11 | 2003-04-09 | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
| PA20038570901A PA8570901A1 (es) | 2002-04-11 | 2003-04-09 | Derivados de acil-4-carboxifenilurea, procedimientos para su preparacion y su uso |
| ARP030101247A AR039403A1 (es) | 2002-04-11 | 2003-04-09 | Derivados de acil-4-carboxifenilurea y su uso como antidiabetico |
| US10/410,601 US7223796B2 (en) | 2002-04-11 | 2003-04-10 | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
| UY27761A UY27761A1 (es) | 2002-04-11 | 2003-04-11 | Derivados de acil-4-carboxifenilurea, procedimientos para su preparcción y su uso. |
| MA27867A MA26390A1 (fr) | 2002-04-11 | 2004-09-20 | Derives d'acyl-4-carboxyphenyluree, procedes pour les preparer et leur utilisation |
| TNP2004000199A TNSN04199A1 (en) | 2002-04-11 | 2004-10-08 | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
| EC2004005347A ECSP045347A (es) | 2002-04-11 | 2004-10-08 | "derivados de acil-4-carboxifenilurea, procedimientos para su preparacion y su uso" |
| NO20044882A NO20044882L (no) | 2002-04-11 | 2004-11-09 | Acyl-4-karboksylfenylurinstoffderivater, deres fremstilling og anvendelse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10215907A DE10215907A1 (de) | 2002-04-11 | 2002-04-11 | Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10215907A1 true DE10215907A1 (de) | 2003-11-06 |
Family
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Family Applications (2)
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| DE10215907A Withdrawn DE10215907A1 (de) | 2002-04-11 | 2002-04-11 | Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
| DE50312949T Expired - Lifetime DE50312949D1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| DE50312949T Expired - Lifetime DE50312949D1 (de) | 2002-04-11 | 2003-03-28 | Acyl-4-carboxy-phenyl-harnstoffderivate, verfahren zu deren herstellung und deren verwendung |
Country Status (28)
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|---|---|
| EP (1) | EP1497262B1 (enExample) |
| JP (1) | JP4328211B2 (enExample) |
| KR (1) | KR20040097333A (enExample) |
| CN (1) | CN1286805C (enExample) |
| AR (1) | AR039403A1 (enExample) |
| AT (1) | ATE476412T1 (enExample) |
| AU (1) | AU2003216900A1 (enExample) |
| BR (1) | BR0309242A (enExample) |
| CA (1) | CA2481817A1 (enExample) |
| DE (2) | DE10215907A1 (enExample) |
| EC (1) | ECSP045347A (enExample) |
| HR (1) | HRPK20040930B3 (enExample) |
| HU (1) | HUP0500440A2 (enExample) |
| IL (1) | IL164249A0 (enExample) |
| MA (1) | MA26390A1 (enExample) |
| MX (1) | MXPA04009468A (enExample) |
| NO (1) | NO20044882L (enExample) |
| NZ (1) | NZ535834A (enExample) |
| OA (1) | OA12805A (enExample) |
| PA (1) | PA8570901A1 (enExample) |
| PE (1) | PE20040374A1 (enExample) |
| PL (1) | PL371279A1 (enExample) |
| RU (1) | RU2004133045A (enExample) |
| TN (1) | TNSN04199A1 (enExample) |
| TW (1) | TW200404762A (enExample) |
| UA (1) | UA78040C2 (enExample) |
| UY (1) | UY27761A1 (enExample) |
| WO (1) | WO2003084922A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10306502B4 (de) * | 2003-02-17 | 2005-03-17 | Aventis Pharma Deutschland Gmbh | Substituierte 3-(Benzoylureido)-thiophenderivate und sie enthaltende Arzneimittel |
| DE10308353A1 (de) | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10308352A1 (de) | 2003-02-27 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Arylcycloalkylderivate mit verzweigten Seitenketten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| US7148246B2 (en) | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
| DE10308351A1 (de) | 2003-02-27 | 2004-11-25 | Aventis Pharma Deutschland Gmbh | 1,3-substituierte Cycloalkylderivate mit sauren, meist heterocyclischen Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10308355A1 (de) | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| US7501440B2 (en) | 2003-03-07 | 2009-03-10 | Sanofi-Aventis Deutschland Gmbh | Substituted benzoylureidopyridylpiperidine-and-pyrrolidinecarboxylic acid derivatives, processes for preparing them and their use |
| DE10309929B4 (de) * | 2003-03-07 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | Substituierte Benzoylureidopyridyl-piperidin- und -pyrrolidin-carbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
| US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
| EP1586573B1 (en) | 2004-04-01 | 2007-02-07 | Sanofi-Aventis Deutschland GmbH | Oxadiazolones, processes for their preparation and their use as pharmaceuticals |
| DE102005026762A1 (de) | 2005-06-09 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Azolopyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen |
| AU2006299091A1 (en) | 2005-09-29 | 2007-04-12 | Sanofi-Aventis | Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007012284A1 (de) | 2007-03-16 | 2008-09-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| DE102007035334A1 (de) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| DE102007035333A1 (de) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007042154A1 (de) | 2007-09-05 | 2009-03-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Arylsulfonylaminomethyphosphonsäure-Derivate, deren Herstellung und deren Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| JP2013503135A (ja) | 2009-08-26 | 2013-01-31 | サノフイ | 新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JP6358942B2 (ja) * | 2014-12-05 | 2018-07-18 | 沢井製薬株式会社 | エンドトキシンの測定用試薬及びエンドトキシンの測定方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0193249A2 (en) * | 1985-03-01 | 1986-09-03 | Duphar International Research B.V | Benzoyl urea derivatives having ati-tumor activity |
| WO2001094300A1 (de) * | 2000-06-09 | 2001-12-13 | Aventis Pharma Deutschland Gmbh | Acylphenylharnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2843851A1 (de) * | 1978-10-07 | 1980-04-17 | Bayer Ag | Substituierte n-benzoyl-n'-tert.-alkoxycarbonylphenyl-(thio)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE3100911A1 (de) * | 1981-01-14 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenylharnstoffe und ihre verwendung zur bekaempfung von insekten |
| DE3217619A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,4-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3217620A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,5-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3478573D1 (en) * | 1983-09-01 | 1989-07-13 | Duphar Int Res | Benzoyl urea derivatives having anti-tumor activity |
| EP0167197B1 (en) * | 1984-07-05 | 1989-01-18 | Duphar International Research B.V | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| DE3722155A1 (de) * | 1987-07-04 | 1989-01-12 | Basf Ag | (n-benzoyl-n'-halogenalkoxycarbonylphenyl)-harnstoffe |
| US6297269B1 (en) * | 1995-06-06 | 2001-10-02 | Pfizer Inc. | Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors |
| AR028253A1 (es) * | 2000-03-16 | 2003-04-30 | Pfizer Prod Inc | Inhibidores de la glucogeno fosforilasa |
| GB0021831D0 (en) * | 2000-09-06 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| TWI236474B (en) * | 2001-04-03 | 2005-07-21 | Telik Inc | Antagonists of MCP-1 function and methods of use thereof |
| PE20021091A1 (es) * | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| DE10215908B4 (de) * | 2002-04-11 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Acyl-3-carboxyphenyl-harnstoffderivate und deren Verwendung als Arzneimittel |
-
2002
- 2002-04-11 IL IL16424902A patent/IL164249A0/xx unknown
- 2002-04-11 DE DE10215907A patent/DE10215907A1/de not_active Withdrawn
-
2003
- 2003-03-28 HU HU0500440A patent/HUP0500440A2/hu unknown
- 2003-03-28 NZ NZ535834A patent/NZ535834A/en unknown
- 2003-03-28 AT AT03712111T patent/ATE476412T1/de active
- 2003-03-28 CA CA002481817A patent/CA2481817A1/en not_active Abandoned
- 2003-03-28 EP EP03712111A patent/EP1497262B1/de not_active Expired - Lifetime
- 2003-03-28 RU RU2004133045/04A patent/RU2004133045A/ru not_active Application Discontinuation
- 2003-03-28 MX MXPA04009468A patent/MXPA04009468A/es unknown
- 2003-03-28 OA OA1200400276A patent/OA12805A/fr unknown
- 2003-03-28 PL PL03371279A patent/PL371279A1/xx not_active Application Discontinuation
- 2003-03-28 UA UA20041109224A patent/UA78040C2/uk unknown
- 2003-03-28 JP JP2003582121A patent/JP4328211B2/ja not_active Expired - Fee Related
- 2003-03-28 AU AU2003216900A patent/AU2003216900A1/en not_active Abandoned
- 2003-03-28 BR BR0309242-9A patent/BR0309242A/pt not_active IP Right Cessation
- 2003-03-28 CN CNB038081873A patent/CN1286805C/zh not_active Expired - Fee Related
- 2003-03-28 KR KR10-2004-7016158A patent/KR20040097333A/ko not_active Withdrawn
- 2003-03-28 HR HR20040930A patent/HRPK20040930B3/xx not_active IP Right Cessation
- 2003-03-28 DE DE50312949T patent/DE50312949D1/de not_active Expired - Lifetime
- 2003-03-28 WO PCT/EP2003/003251 patent/WO2003084922A1/de not_active Ceased
- 2003-04-07 PE PE2003000349A patent/PE20040374A1/es not_active Application Discontinuation
- 2003-04-09 PA PA20038570901A patent/PA8570901A1/es unknown
- 2003-04-09 TW TW092108057A patent/TW200404762A/zh unknown
- 2003-04-09 AR ARP030101247A patent/AR039403A1/es unknown
- 2003-04-11 UY UY27761A patent/UY27761A1/es unknown
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2004
- 2004-09-20 MA MA27867A patent/MA26390A1/fr unknown
- 2004-10-08 EC EC2004005347A patent/ECSP045347A/es unknown
- 2004-10-08 TN TNP2004000199A patent/TNSN04199A1/en unknown
- 2004-11-09 NO NO20044882A patent/NO20044882L/no unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0193249A2 (en) * | 1985-03-01 | 1986-09-03 | Duphar International Research B.V | Benzoyl urea derivatives having ati-tumor activity |
| WO2001094300A1 (de) * | 2000-06-09 | 2001-12-13 | Aventis Pharma Deutschland Gmbh | Acylphenylharnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts 109:18749 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE476412T1 (de) | 2010-08-15 |
| KR20040097333A (ko) | 2004-11-17 |
| BR0309242A (pt) | 2005-02-09 |
| CN1286805C (zh) | 2006-11-29 |
| IL164249A0 (en) | 2005-12-18 |
| WO2003084922A8 (de) | 2005-01-13 |
| UY27761A1 (es) | 2003-10-31 |
| AU2003216900A1 (en) | 2003-10-20 |
| NZ535834A (en) | 2006-07-28 |
| EP1497262B1 (de) | 2010-08-04 |
| ECSP045347A (es) | 2004-11-26 |
| HUP0500440A2 (hu) | 2005-08-29 |
| NO20044882L (no) | 2004-11-09 |
| HRPK20040930B3 (en) | 2006-09-30 |
| RU2004133045A (ru) | 2005-05-27 |
| TNSN04199A1 (en) | 2007-03-12 |
| HRP20040930A2 (en) | 2005-04-30 |
| CN1646485A (zh) | 2005-07-27 |
| PE20040374A1 (es) | 2004-07-20 |
| MXPA04009468A (es) | 2005-01-25 |
| JP2005522480A (ja) | 2005-07-28 |
| OA12805A (fr) | 2006-07-11 |
| PA8570901A1 (es) | 2003-11-12 |
| TW200404762A (en) | 2004-04-01 |
| UA78040C2 (en) | 2007-02-15 |
| EP1497262A1 (de) | 2005-01-19 |
| CA2481817A1 (en) | 2003-10-16 |
| JP4328211B2 (ja) | 2009-09-09 |
| AR039403A1 (es) | 2005-02-16 |
| DE50312949D1 (de) | 2010-09-16 |
| PL371279A1 (en) | 2005-06-13 |
| MA26390A1 (fr) | 2004-11-01 |
| WO2003084922A1 (de) | 2003-10-16 |
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