DE102008019907A1 - Pyridazinonderivate - Google Patents
Pyridazinonderivate Download PDFInfo
- Publication number
- DE102008019907A1 DE102008019907A1 DE102008019907A DE102008019907A DE102008019907A1 DE 102008019907 A1 DE102008019907 A1 DE 102008019907A1 DE 102008019907 A DE102008019907 A DE 102008019907A DE 102008019907 A DE102008019907 A DE 102008019907A DE 102008019907 A1 DE102008019907 A1 DE 102008019907A1
- Authority
- DE
- Germany
- Prior art keywords
- diyl
- het
- salts
- solvates
- stereoisomers
- 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- Withdrawn
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 9
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- FPYJSJDOHRDAMT-KQWNVCNZSA-N 1h-indole-5-sulfonamide, n-(3-chlorophenyl)-3-[[3,5-dimethyl-4-[(4-methyl-1-piperazinyl)carbonyl]-1h-pyrrol-2-yl]methylene]-2,3-dihydro-n-methyl-2-oxo-, (3z)- Chemical compound C=1C=C2NC(=O)\C(=C/C3=C(C(C(=O)N4CCN(C)CC4)=C(C)N3)C)C2=CC=1S(=O)(=O)N(C)C1=CC=CC(Cl)=C1 FPYJSJDOHRDAMT-KQWNVCNZSA-N 0.000 claims abstract description 20
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- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 9
- -1 thiophenediyl Chemical group 0.000 claims description 226
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- VCOVBJXJBKJWCP-UHFFFAOYSA-N 6-(3-methylphenyl)-2-[[4-[5-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]pyrimidin-2-yl]thiophen-2-yl]methyl]pyridazin-3-one Chemical compound CC1=CC=CC(C2=NN(CC=3SC=C(C=3)C=3N=CC(=CN=3)C3=CN(CCN4CCCC4)N=C3)C(=O)C=C2)=C1 VCOVBJXJBKJWCP-UHFFFAOYSA-N 0.000 claims description 4
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- RGCZVQOSRVUDLG-UHFFFAOYSA-N 6-(3-methylphenyl)-2-[[6-[5-[(1-methylpiperidin-4-yl)methoxy]pyrimidin-2-yl]pyridin-2-yl]methyl]pyridazin-3-one Chemical compound C1CN(C)CCC1COC1=CN=C(C=2N=C(CN3C(C=CC(=N3)C=3C=C(C)C=CC=3)=O)C=CC=2)N=C1 RGCZVQOSRVUDLG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008019907A DE102008019907A1 (de) | 2008-04-21 | 2008-04-21 | Pyridazinonderivate |
| PCT/EP2009/002137 WO2009129905A1 (de) | 2008-04-21 | 2009-03-24 | Pyridazinonderivate |
| EP09734854A EP2280962B1 (de) | 2008-04-21 | 2009-03-24 | Pyridazinonderivate |
| AU2009240346A AU2009240346B2 (en) | 2008-04-21 | 2009-03-24 | Pyridazinone derivatives |
| PT97348544T PT2280962E (pt) | 2008-04-21 | 2009-03-24 | Derivados de piridazinona |
| CA2721858A CA2721858C (en) | 2008-04-21 | 2009-03-24 | Pyridazinone derivatives |
| KR1020107025412A KR20100137564A (ko) | 2008-04-21 | 2009-03-24 | 피리다지논 유도체 |
| HRP20120884AT HRP20120884T1 (hr) | 2008-04-21 | 2009-03-24 | Derivati piridazinona |
| SI200930411T SI2280962T1 (sl) | 2008-04-21 | 2009-03-24 | Derivati piridazinona |
| EA201001648A EA018362B1 (ru) | 2008-04-21 | 2009-03-24 | Производные пиридазинона |
| US12/988,666 US8604036B2 (en) | 2008-04-21 | 2009-03-24 | Pyridazinone derivatives |
| MX2010011454A MX2010011454A (es) | 2008-04-21 | 2009-03-24 | Derivados de piridazinona. |
| DK09734854.4T DK2280962T5 (da) | 2008-04-21 | 2009-03-24 | Pyridazinonderivater |
| BRPI0911161A BRPI0911161B8 (pt) | 2008-04-21 | 2009-03-24 | derivados de piridazinona e seu processo de preparação |
| ES09734854T ES2394147T3 (es) | 2008-04-21 | 2009-03-24 | Derivados de piridazinona |
| JP2011505385A JP5576358B2 (ja) | 2008-04-21 | 2009-03-24 | ピリダジノン誘導体 |
| PL09734854T PL2280962T3 (pl) | 2008-04-21 | 2009-03-24 | Pochodne pirydazynonowe |
| CN2009801141150A CN102015694A (zh) | 2008-04-21 | 2009-03-24 | 哒嗪酮衍生物 |
| ARP090101359A AR071208A1 (es) | 2008-04-21 | 2009-04-17 | Derivados de piridazinona |
| IL208336A IL208336A (en) | 2008-04-21 | 2010-09-21 | Pyridazinone derivatives, drugs containing them and their uses and process for preparation |
| ZA2010/08330A ZA201008330B (en) | 2008-04-21 | 2010-11-19 | Pyridazinone derivatives |
| CY20121101191T CY1113443T1 (el) | 2008-04-21 | 2012-12-07 | Παραγωγα πυριδαζινονης |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008019907A DE102008019907A1 (de) | 2008-04-21 | 2008-04-21 | Pyridazinonderivate |
Publications (1)
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| DE102008019907A1 true DE102008019907A1 (de) | 2009-10-22 |
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Family Applications (1)
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| DE102008019907A Withdrawn DE102008019907A1 (de) | 2008-04-21 | 2008-04-21 | Pyridazinonderivate |
Country Status (22)
| Country | Link |
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| US (1) | US8604036B2 (https=) |
| EP (1) | EP2280962B1 (https=) |
| JP (1) | JP5576358B2 (https=) |
| KR (1) | KR20100137564A (https=) |
| CN (1) | CN102015694A (https=) |
| AR (1) | AR071208A1 (https=) |
| AU (1) | AU2009240346B2 (https=) |
| BR (1) | BRPI0911161B8 (https=) |
| CA (1) | CA2721858C (https=) |
| CY (1) | CY1113443T1 (https=) |
| DE (1) | DE102008019907A1 (https=) |
| DK (1) | DK2280962T5 (https=) |
| EA (1) | EA018362B1 (https=) |
| ES (1) | ES2394147T3 (https=) |
| HR (1) | HRP20120884T1 (https=) |
| IL (1) | IL208336A (https=) |
| MX (1) | MX2010011454A (https=) |
| PL (1) | PL2280962T3 (https=) |
| PT (1) | PT2280962E (https=) |
| SI (1) | SI2280962T1 (https=) |
| WO (1) | WO2009129905A1 (https=) |
| ZA (1) | ZA201008330B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102007038957A1 (de) * | 2007-08-17 | 2009-02-19 | Merck Patent Gmbh | 6-Thioxo-pyridazinderivate |
| DE102007061963A1 (de) * | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008019907A1 (de) | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008028905A1 (de) * | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| DE102008037790A1 (de) * | 2008-08-14 | 2010-02-18 | Merck Patent Gmbh | Bicyclische Triazolderivate |
| SI2361250T1 (sl) | 2008-12-22 | 2013-12-31 | Merck Patent Gmbh | Nove polimorfne oblike 6-(1-metil-1h-pirazol-4-il)-2-(3-(5-(2-morfolin-4-il-etoksi)-pirimidin- 2-il)-benzil)-2h-piridazin-3-on dihidrogenfosfata in postopki za proizvodnjo le-tega |
| CN102532126B (zh) * | 2012-02-10 | 2014-06-18 | 贵州大学 | 2-取代-4-氯-5-[5-取代胺基-2-(1,3,4-噻二唑基)-巯基]-3(2h)-哒嗪酮类衍生物及其制备方法和用途 |
| WO2018081381A1 (en) * | 2016-10-26 | 2018-05-03 | Proteostasis Therapeutics, Inc | Pyridazine derivatives, compositions and methods for modulating cftr |
| US11180480B2 (en) | 2017-10-17 | 2021-11-23 | Sensorion | Synthesis of 4-aminopyrimidine compounds |
| CN108752322A (zh) * | 2018-09-12 | 2018-11-06 | 广州新民培林医药科技有限公司 | 一种新型Tepotinib衍生物和制备方法及其在抗肿瘤药物中的应用 |
| ES2958954T3 (es) | 2018-11-06 | 2024-02-16 | Edgewise Therapeutics Inc | Compuestos de piridazinona y usos de los mismos |
| WO2020097258A1 (en) | 2018-11-06 | 2020-05-14 | Edgewise Therapeutics, Inc. | Pyridazinone compounds and uses thereof |
| EP3877052B1 (en) | 2018-11-06 | 2023-08-16 | Edgewise Therapeutics, Inc. | Pyridazinone compounds and uses thereof |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN114502551B (zh) | 2019-11-01 | 2023-08-22 | 优迈特株式会社 | 含氟嘧啶化合物及其制备方法 |
Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5795964A (en) | 1980-12-04 | 1982-06-15 | Morishita Seiyaku Kk | Preparation of 2-substituted-3(2h)-pyridazinone derivative |
| US4397854A (en) | 1981-05-14 | 1983-08-09 | Warner-Lambert Company | Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents |
| EP0738716A2 (en) | 1995-04-21 | 1996-10-23 | Rohm And Haas Company | Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides |
| WO1997022596A1 (en) | 1995-12-18 | 1997-06-26 | Zeneca Limited | Quinazoline derivatives |
| WO1997030035A1 (en) | 1996-02-13 | 1997-08-21 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| WO1997032856A1 (en) | 1996-03-05 | 1997-09-12 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| WO1998013354A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Quinazoline derivatives and pharmaceutical compositions containing them |
| WO1999002166A1 (en) | 1997-07-08 | 1999-01-21 | Angiogene Pharmaceuticals Ltd. | Use of colchinol derivatives as vascular damaging agents |
| WO2000040529A1 (en) | 1999-01-07 | 2000-07-13 | Angiogene Pharmaceuticals Ltd. | Colchinol derivatives as vascular damaging agents |
| WO2000041669A2 (en) | 1999-01-15 | 2000-07-20 | Angiogene Pharmaceuticals Ltd. | Benzimidazole vascular damaging agents |
| EP1043317A1 (en) | 1997-11-19 | 2000-10-11 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| EP1061077A1 (en) | 1998-03-02 | 2000-12-20 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| WO2001092224A1 (en) | 2000-05-31 | 2001-12-06 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| EP0711759B1 (en) | 1994-11-14 | 2002-01-09 | Dow AgroSciences LLC | Pyridazinones and their use as fungicides |
| WO2002004434A1 (en) | 2000-07-07 | 2002-01-17 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as vascular damaging agents |
| WO2002008213A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| WO2003037349A1 (en) | 2001-10-31 | 2003-05-08 | Merck Patent Gmbh | Type 4 phosphodiesterase inhibitors and uses thereof |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19604388A1 (de) | 1996-02-07 | 1997-08-14 | Merck Patent Gmbh | Arylalkyl-diazinone |
| JPH10259176A (ja) | 1997-03-17 | 1998-09-29 | Japan Tobacco Inc | 血管新生阻害作用を有する新規アミド誘導体及びその用途 |
| CA2340230C (en) * | 1998-08-14 | 2008-03-11 | Nihon Nohyaku Co., Ltd. | Pyridazinone derivatives having cell adhesion inhibiting activity |
| AUPQ462299A0 (en) * | 1999-12-13 | 2000-01-13 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| US6242461B1 (en) * | 2000-01-25 | 2001-06-05 | Pfizer Inc. | Use of aryl substituted azabenzimidazoles in the treatment of HIV and AIDS related diseases |
| ZA200504898B (en) | 2002-12-20 | 2006-11-29 | Pharmacia Corp | Acyclic pyrazole compounds |
| JP2007516180A (ja) | 2003-07-02 | 2007-06-21 | スゲン，インコーポレイティド | ｃ−Ｍｅｔ阻害薬としてのアリールメチルトリアゾロおよびイミダゾピラジン類 |
| US7959919B2 (en) * | 2003-11-19 | 2011-06-14 | Novelmed Therapeutics, Inc. | Method of inhibiting factor B-mediated complement activation |
| TW200612918A (en) | 2004-07-29 | 2006-05-01 | Threshold Pharmaceuticals Inc | Lonidamine analogs |
| US20070015771A1 (en) * | 2004-07-29 | 2007-01-18 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| US20070043057A1 (en) * | 2005-02-09 | 2007-02-22 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| WO2007044796A2 (en) | 2005-10-11 | 2007-04-19 | Nps Pharmaceuticals, Inc. | Pyridazinone compounds as calcilytics |
| KR20080080584A (ko) | 2005-11-30 | 2008-09-04 | 버텍스 파마슈티칼스 인코포레이티드 | ｃ-Ｍｅｔ의 억제제 및 이의 용도 |
| DE102005057924A1 (de) * | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Pyridazinonderivate |
| HRP20170103T1 (hr) * | 2005-12-21 | 2017-03-24 | Janssen Pharmaceutica N.V. | Triazolopiridazini kao modulatori tirozin kinaze |
| WO2007130383A2 (en) | 2006-04-28 | 2007-11-15 | Northwestern University | Compositions and treatments using pyridazine compounds and secretases |
| NL2000613C2 (nl) | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazoolpyrazinederivaten. |
| GB0610680D0 (en) * | 2006-05-31 | 2006-07-12 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| PE20080403A1 (es) | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| DE102006037478A1 (de) * | 2006-08-10 | 2008-02-14 | Merck Patent Gmbh | 2-(Heterocyclylbenzyl)-pyridazinonderivate |
| US7737149B2 (en) | 2006-12-21 | 2010-06-15 | Astrazeneca Ab | N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof |
| MX2009008531A (es) * | 2007-02-16 | 2009-08-26 | Amgen Inc | Cetonas de heterociclilo que contienen nitrogeno y su uso como inhibidores de c-met. |
| DE102007026341A1 (de) * | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) * | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| JP2011500629A (ja) | 2007-10-16 | 2011-01-06 | ノバルティス アーゲー | 神経ペプチドｙ２受容体のモジュレーターとしての置換ピペラジンおよびピペリジン |
| JP2011500778A (ja) | 2007-10-25 | 2011-01-06 | アストラゼネカ・アクチエボラーグ | ピリジン及びピラジン誘導体−０８３ |
| WO2009057827A1 (en) * | 2007-10-31 | 2009-05-07 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives and use thereof as p2x7 receptor inhibitors |
| TW200927115A (en) | 2007-11-16 | 2009-07-01 | Boehringer Ingelheim Int | Aryl-and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| US7816540B2 (en) | 2007-12-21 | 2010-10-19 | Hoffmann-La Roche Inc. | Carboxyl- or hydroxyl-substituted benzimidazole derivatives |
| CN101903385B (zh) | 2007-12-21 | 2013-11-06 | 帕劳制药股份有限公司 | 作为组胺h4受体拮抗剂的4-氨基嘧啶衍生物 |
| US8202996B2 (en) | 2007-12-21 | 2012-06-19 | Bristol-Myers Squibb Company | Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-chloro-4-methoxy-1-isoquinolinyl)oxy)-N- ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide |
| WO2009080534A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| EP2072506A1 (de) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Thiazolyloxyphenylamidine oder Thiadiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| CA2709514A1 (en) | 2007-12-21 | 2009-07-02 | Astrazeneca Ab | Bicyclic derivatives for use in the treatment of androgen receptor associated conditions |
| AU2008340421B2 (en) | 2007-12-21 | 2013-12-19 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| EP2242483B1 (en) | 2007-12-21 | 2013-02-20 | Synthon B.V. | Raloxifene composition |
| PE20091339A1 (es) | 2007-12-21 | 2009-09-26 | Glaxo Group Ltd | Derivados de oxadiazol con actividad sobre receptores s1p1 |
| AR069869A1 (es) | 2007-12-21 | 2010-02-24 | Exelixis Inc | Derivados de benzofuro[3,2-d]pirimidinas inhibidores de proteinquinasas,composiciones farmaceuticas que los comprenden y usos de los mismos en el tratamiento del cancer. |
| CL2008003785A1 (es) | 2007-12-21 | 2009-10-09 | Du Pont | Compuestos derivados de piridazina; composiciones herbicidas que comprenden a dichos compuestos; y método para controlar el crecimiento de la vegetación indeseada. |
| DE102007061963A1 (de) * | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| GB0725059D0 (en) | 2007-12-21 | 2008-01-30 | Syngenta Participations Ag | Novel pyridazine derivatives |
| CN101537006B (zh) * | 2008-03-18 | 2012-06-06 | 中国科学院上海药物研究所 | 哒嗪酮类化合物在制备抗肿瘤药物中的用途 |
| DE102008019907A1 (de) | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| WO2009142732A2 (en) * | 2008-05-20 | 2009-11-26 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
| DE102008028905A1 (de) * | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| EP2323994A1 (en) * | 2008-07-25 | 2011-05-25 | Boehringer Ingelheim International GmbH | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| BRPI1013159A2 (pt) * | 2009-03-30 | 2015-09-15 | Sumitomo Chemical Co | Uso de composto de piridazinona para controle de peste artrópode |
| AR082590A1 (es) * | 2010-08-12 | 2012-12-19 | Hoffmann La Roche | Inhibidores de la tirosina-quinasa de bruton |
-
2008
- 2008-04-21 DE DE102008019907A patent/DE102008019907A1/de not_active Withdrawn
-
2009
- 2009-03-24 WO PCT/EP2009/002137 patent/WO2009129905A1/de not_active Ceased
- 2009-03-24 ES ES09734854T patent/ES2394147T3/es active Active
- 2009-03-24 US US12/988,666 patent/US8604036B2/en not_active Expired - Fee Related
- 2009-03-24 HR HRP20120884AT patent/HRP20120884T1/hr unknown
- 2009-03-24 DK DK09734854.4T patent/DK2280962T5/da active
- 2009-03-24 MX MX2010011454A patent/MX2010011454A/es active IP Right Grant
- 2009-03-24 PT PT97348544T patent/PT2280962E/pt unknown
- 2009-03-24 AU AU2009240346A patent/AU2009240346B2/en not_active Ceased
- 2009-03-24 JP JP2011505385A patent/JP5576358B2/ja not_active Expired - Fee Related
- 2009-03-24 CN CN2009801141150A patent/CN102015694A/zh active Pending
- 2009-03-24 CA CA2721858A patent/CA2721858C/en active Active
- 2009-03-24 KR KR1020107025412A patent/KR20100137564A/ko not_active Ceased
- 2009-03-24 PL PL09734854T patent/PL2280962T3/pl unknown
- 2009-03-24 BR BRPI0911161A patent/BRPI0911161B8/pt not_active IP Right Cessation
- 2009-03-24 EA EA201001648A patent/EA018362B1/ru not_active IP Right Cessation
- 2009-03-24 EP EP09734854A patent/EP2280962B1/de active Active
- 2009-03-24 SI SI200930411T patent/SI2280962T1/sl unknown
- 2009-04-17 AR ARP090101359A patent/AR071208A1/es not_active Application Discontinuation
-
2010
- 2010-09-21 IL IL208336A patent/IL208336A/en active IP Right Grant
- 2010-11-19 ZA ZA2010/08330A patent/ZA201008330B/en unknown
-
2012
- 2012-12-07 CY CY20121101191T patent/CY1113443T1/el unknown
Patent Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5795964A (en) | 1980-12-04 | 1982-06-15 | Morishita Seiyaku Kk | Preparation of 2-substituted-3(2h)-pyridazinone derivative |
| US4397854A (en) | 1981-05-14 | 1983-08-09 | Warner-Lambert Company | Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents |
| EP0711759B1 (en) | 1994-11-14 | 2002-01-09 | Dow AgroSciences LLC | Pyridazinones and their use as fungicides |
| EP0738716A2 (en) | 1995-04-21 | 1996-10-23 | Rohm And Haas Company | Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides |
| WO1997022596A1 (en) | 1995-12-18 | 1997-06-26 | Zeneca Limited | Quinazoline derivatives |
| WO1997030035A1 (en) | 1996-02-13 | 1997-08-21 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| WO1997032856A1 (en) | 1996-03-05 | 1997-09-12 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| WO1998013354A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Quinazoline derivatives and pharmaceutical compositions containing them |
| WO1999002166A1 (en) | 1997-07-08 | 1999-01-21 | Angiogene Pharmaceuticals Ltd. | Use of colchinol derivatives as vascular damaging agents |
| EP1043317A1 (en) | 1997-11-19 | 2000-10-11 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| EP1061077A1 (en) | 1998-03-02 | 2000-12-20 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| WO2000040529A1 (en) | 1999-01-07 | 2000-07-13 | Angiogene Pharmaceuticals Ltd. | Colchinol derivatives as vascular damaging agents |
| WO2000041669A2 (en) | 1999-01-15 | 2000-07-20 | Angiogene Pharmaceuticals Ltd. | Benzimidazole vascular damaging agents |
| WO2001092224A1 (en) | 2000-05-31 | 2001-12-06 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| WO2002004434A1 (en) | 2000-07-07 | 2002-01-17 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as vascular damaging agents |
| WO2002008213A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| WO2003037349A1 (en) | 2001-10-31 | 2003-05-08 | Merck Patent Gmbh | Type 4 phosphodiesterase inhibitors and uses thereof |
Non-Patent Citations (21)
| Title |
|---|
| Alessi et al., FEBS Lett. 1996, 399, 3, Seiten 333-338 |
| Ausprunk et al., Dev. Biol. 38: 237-248 |
| Campos-González, R. und Glenney, Jr., J. R. 1992, J. Biol. Chem. 267, Seite 14535 |
| Dhanabal et al., Cancer Res. 59: 189-197 |
| Gimbrone et al., J. Natl. Cancer Inst. 52: 413-427 |
| H. Hov et al. in Clinical Cancer Research Vol. 10, 6686-6694 (2004) |
| Houben-Weyl, Methoden der organischen Chemie, Georg-Thieme-Verlag, Stuttgart |
| Int. J. Pharm. 115, 61-67 (1995) |
| J. G. Christensen et al. in Cancer Res. 2003, 63(21), 7345-55 |
| Khwaja et al., EMBO, 1997, 16, 2783-93 |
| Nicosia et al., In Vitro 18: 538-549 |
| Ross et al., 2002, Biochem. J. |
| S. Serthou et al. in Oncogene, Vol. 23, Nr. 31, Seiten 5387-5393 (2004) |
| Sheu et al., Anticancer Res. 18: 4435-4441 |
| Sills et al., J. of Biomolecular Screening, 2002, 191-214 |
| Sorg et al., J. of. Biomolecular Screening, 2002, 7, 11-19 |
| Stephens et al., Biochemical J., 2000, 351, 95-105 |
| W. J. Coates, A. McKillop, Synthesis, 1993, 334-342 |
| Weinstein-Oppenheimer et al. Pharma. &. Therap., 2000, 88, 229-279 |
| White et al., Oncogene, 2001, 20, 7064-7072 |
| Xin et al., J. Biol. Chem. 274: 9116-9121 |
Also Published As
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| MX2010011454A (es) | 2010-12-21 |
| IL208336A (en) | 2016-07-31 |
| IL208336A0 (en) | 2010-12-30 |
| CA2721858C (en) | 2016-07-19 |
| BRPI0911161A2 (pt) | 2015-10-06 |
| EP2280962B1 (de) | 2012-10-03 |
| DK2280962T3 (da) | 2012-11-19 |
| BRPI0911161B8 (pt) | 2021-05-25 |
| US20110034474A1 (en) | 2011-02-10 |
| CY1113443T1 (el) | 2016-06-22 |
| WO2009129905A1 (de) | 2009-10-29 |
| ES2394147T3 (es) | 2013-01-22 |
| EA201001648A1 (ru) | 2011-06-30 |
| PT2280962E (pt) | 2012-12-17 |
| SI2280962T1 (sl) | 2013-01-31 |
| EA018362B1 (ru) | 2013-07-30 |
| CN102015694A (zh) | 2011-04-13 |
| KR20100137564A (ko) | 2010-12-30 |
| HRP20120884T1 (hr) | 2012-11-30 |
| AR071208A1 (es) | 2010-06-02 |
| DK2280962T5 (da) | 2013-09-16 |
| EP2280962A1 (de) | 2011-02-09 |
| US8604036B2 (en) | 2013-12-10 |
| CA2721858A1 (en) | 2009-10-29 |
| AU2009240346A1 (en) | 2009-10-29 |
| PL2280962T3 (pl) | 2013-02-28 |
| JP5576358B2 (ja) | 2014-08-20 |
| JP2011518202A (ja) | 2011-06-23 |
| AU2009240346B2 (en) | 2013-10-10 |
| BRPI0911161B1 (pt) | 2020-02-11 |
| ZA201008330B (en) | 2011-09-28 |
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