HRP20050198A2 - Piperidin-piridazoni i ftalazoni kao inhibitori pde4 - Google Patents
Piperidin-piridazoni i ftalazoni kao inhibitori pde4Info
- Publication number
- HRP20050198A2 HRP20050198A2 HR20050198A HRP20050198A HRP20050198A2 HR P20050198 A2 HRP20050198 A2 HR P20050198A2 HR 20050198 A HR20050198 A HR 20050198A HR P20050198 A HRP20050198 A HR P20050198A HR P20050198 A2 HRP20050198 A2 HR P20050198A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkoxy
- hydrogen
- alkyl
- integer
- formula
- Prior art date
Links
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title claims abstract description 11
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title claims abstract description 11
- KHSHUCGBOGKFDA-UHFFFAOYSA-N piperidine;1h-pyridazin-6-one Chemical class C1CCNCC1.O=C1C=CC=NN1 KHSHUCGBOGKFDA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- -1 cinolinyl Chemical group 0.000 claims description 229
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 123
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 62
- 150000002431 hydrogen Chemical group 0.000 claims description 57
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 56
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 56
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 56
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 56
- 125000002971 oxazolyl group Chemical group 0.000 claims description 56
- 125000001544 thienyl group Chemical group 0.000 claims description 56
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 55
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 55
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims description 50
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 239000011737 fluorine Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000002541 furyl group Chemical group 0.000 claims description 42
- 125000002883 imidazolyl group Chemical group 0.000 claims description 42
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 42
- 125000001041 indolyl group Chemical group 0.000 claims description 42
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 42
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 42
- 125000005493 quinolyl group Chemical group 0.000 claims description 42
- 125000000335 thiazolyl group Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 30
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 30
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 30
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 30
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 28
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 28
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
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- 238000000034 method Methods 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 14
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
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- 239000001301 oxygen Substances 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical group C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 5
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- A—HUMAN NECESSITIES
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- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P37/08—Antiallergic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02017977 | 2002-08-10 | ||
| PCT/EP2003/008724 WO2004017974A1 (en) | 2002-08-10 | 2003-08-06 | Piperidine-pyridazones and phthalazones as pde4 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20050198A2 true HRP20050198A2 (hr) | 2006-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20050198A HRP20050198A2 (hr) | 2002-08-10 | 2005-03-01 | Piperidin-piridazoni i ftalazoni kao inhibitori pde4 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7220746B2 (de) |
| EP (2) | EP1537100B1 (de) |
| JP (2) | JP4555684B2 (de) |
| KR (1) | KR101131684B1 (de) |
| CN (1) | CN1671695A (de) |
| AT (1) | ATE360627T1 (de) |
| AU (2) | AU2003258576B2 (de) |
| BR (1) | BR0313330A (de) |
| CA (2) | CA2494613C (de) |
| DE (1) | DE60313472T2 (de) |
| ES (1) | ES2286491T3 (de) |
| HR (1) | HRP20050198A2 (de) |
| IL (1) | IL166271A (de) |
| IS (2) | IS2416B (de) |
| MX (1) | MXPA05001354A (de) |
| PL (2) | PL214701B1 (de) |
| RS (1) | RS51445B (de) |
| WO (2) | WO2004017974A1 (de) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PL363391A1 (en) | 2001-02-15 | 2004-11-15 | Altana Pharma Ag | Phthalayinone-piperidino-derivatives as pde4 inhibitors |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| US7470791B2 (en) | 2003-03-10 | 2008-12-30 | Nycomed Gmbh | Process for the preparation of roflumilast |
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| WO2005075437A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Pyridazinone derivatives and their use as pde4 inhibitors |
| US7494990B2 (en) | 2004-02-04 | 2009-02-24 | Nycomed Gmbh | 2-(piperidin-4-yl)-4,5-dihydro-2H-pyridazin-3-one derivatives as PDE4 inhibitors |
| JP2007536350A (ja) * | 2004-05-10 | 2007-12-13 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 肺気腫の予防又は治療のためのロフルミラストの使用 |
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| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| ES2421916T3 (es) | 2005-03-16 | 2013-09-06 | Nycomed Gmbh | Forma farmacéutica de sabor enmascarado que contiene roflumilast |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| CA2625664C (en) | 2005-10-21 | 2016-01-05 | Novartis Ag | Human antibodies against il13 and therapeutic uses |
| GB0526244D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| ATE549337T1 (de) | 2006-04-21 | 2012-03-15 | Novartis Ag | Purinderivate zur verwendung als adenosin-a2a- rezeptoragonisten |
| WO2008037477A1 (en) | 2006-09-29 | 2008-04-03 | Novartis Ag | Pyrazolopyrimidines as p13k lipid kinase inhibitors |
| AU2007315234A1 (en) | 2006-10-30 | 2008-05-08 | Novartis Ag | Heterocyclic compounds as antiinflammatory agents |
| PL2104535T3 (pl) | 2007-01-10 | 2011-05-31 | Irm Llc | Związki i kompozycje jako inhibitory proteazy aktywujące kanały |
| US8217202B2 (en) * | 2007-04-11 | 2012-07-10 | New Mexico Highlands University | Single carbon precursor synthons |
| ES2361595T3 (es) | 2007-05-07 | 2011-06-20 | Novartis Ag | Compuestos orgánicos. |
| WO2008138939A1 (en) * | 2007-05-16 | 2008-11-20 | Nycomed Gmbh | Pyrazolone derivatives as pde4 inhibitors |
| MX2010006421A (es) | 2007-12-10 | 2010-06-25 | Novartis Ag | Compuestos organicos. |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| BRPI0915018A2 (pt) | 2008-06-10 | 2015-10-27 | Novartis Ag | compostos orgânicos |
| AR074318A1 (es) | 2008-11-14 | 2011-01-05 | Nycomed Gmbh | Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias. |
| WO2010088335A1 (en) | 2009-01-29 | 2010-08-05 | Novartis Ag | Substituted benzimidazoles for the treatment of astrocytomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| BR112012003262A8 (pt) | 2009-08-12 | 2016-05-17 | Novartis Ag | compostos de hidrazona heterocíclica e seus usos para tratar câncer e inflamação |
| IN2012DN01961A (de) | 2009-08-17 | 2015-08-21 | Intellikine Llc | |
| CA2771432A1 (en) | 2009-08-20 | 2011-02-24 | Novartis Ag | Heterocyclic oxime compounds |
| EP2490687A1 (de) | 2009-10-22 | 2012-08-29 | Vertex Pharmaceuticals Incorporated | Zusammensetzungen für die behandlung von mukoviszidose und anderen chronischen erkrankungen |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| EP2678016B1 (de) | 2011-02-23 | 2016-08-10 | Intellikine, LLC | Heterocyclische verbindungen und ihre verwendung |
| BR112013021638A2 (pt) | 2011-02-25 | 2016-08-02 | Irm Llc | "compostos inibidores de trk, seu uso e composições que os compreendem" |
| US20140112945A1 (en) * | 2011-06-17 | 2014-04-24 | Takeda Gmbh | Novel phthalazinone-pyrrolopyrimidinecarboxamide derivatives |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| MX339302B (es) | 2011-09-15 | 2016-05-19 | Novartis Ag | 3-(quinolin-6-il-tio)-[1,2,4]-triazolo-[4,3-a]-piridinas 6-sustituidas como cinasas de tirosina. |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038386A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Heterocyclic compounds for the treatment of cystic fibrosis |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| JP6165733B2 (ja) | 2011-09-16 | 2017-07-19 | ノバルティス アーゲー | Ｎ−置換ヘテロシクリルカルボキサミド類 |
| WO2013078440A2 (en) | 2011-11-23 | 2013-05-30 | Intellikine, Llc | Enhanced treatment regimens using mtor inhibitors |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| ES2894830T3 (es) | 2012-04-03 | 2022-02-16 | Novartis Ag | Productos combinados con inhibidores de tirosina·cinasa y su uso |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| WO2014151147A1 (en) | 2013-03-15 | 2014-09-25 | Intellikine, Llc | Combination of kinase inhibitors and uses thereof |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| MX2016013981A (es) | 2014-04-24 | 2016-11-15 | Novartis Ag | Derivados de amino-piridina como inhibidores de fosfatidil-inositol-3-cinasa. |
| JP6404944B2 (ja) | 2014-04-24 | 2018-10-17 | ノバルティス アーゲー | ホスファチジルイノシトール３−キナーゼ阻害薬としてのピラジン誘導体 |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| US10195208B2 (en) | 2014-07-31 | 2019-02-05 | Novartis Ag | Combination therapy |
| KR20220019015A (ko) | 2019-06-10 | 2022-02-15 | 노파르티스 아게 | Cf, copd, 및 기관지확장증 치료를 위한 피리딘 및 피라진 유도체 |
| CN110330465B (zh) * | 2019-06-28 | 2021-05-11 | 深圳市三启药物开发有限公司 | 腙酰胺类衍生物及其在制备防治脱发药物中的应用 |
| WO2021038426A1 (en) | 2019-08-28 | 2021-03-04 | Novartis Ag | Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease |
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| US5376656A (en) * | 1990-10-16 | 1994-12-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Arylpyridazinones |
| IL103388A (en) | 1991-10-09 | 1997-09-30 | Syntex Inc | PYRIDO £2,3-d| PYRIDAZINONES AND PYRIDAZINETHIONES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| US5716954A (en) * | 1991-10-09 | 1998-02-10 | Syntex U.S.A. Inc. | Benzopyridazinone and pyridopyridazinone compounds |
| WO1994012461A1 (en) | 1992-12-02 | 1994-06-09 | Pfizer Inc. | Catechol diethers as selective pdeiv inhibitors |
| DE19533975A1 (de) | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| US5658940A (en) * | 1995-10-06 | 1997-08-19 | Celgene Corporation | Succinimide and maleimide cytokine inhibitors |
| PT971901E (pt) * | 1997-01-15 | 2003-07-31 | Altana Pharma Ag | Ftalazinonas |
| AU1760399A (en) | 1997-12-15 | 1999-07-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
| AU753576B2 (en) | 1997-12-15 | 2002-10-24 | Altana Pharma Ag | Dihydrobenzofurans |
| EP1070056B1 (de) | 1998-03-14 | 2004-06-30 | ALTANA Pharma AG | Phthalazinone pde iii/iv hemmer |
| AU7654200A (en) | 1999-09-14 | 2001-04-17 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone derivatives as pd3/4 inhibitors |
| ATE374189T1 (de) | 1999-10-25 | 2007-10-15 | Nycomed Gmbh | Phthalazinon-derivate als pde 4 hemmer |
| IL148807A0 (en) * | 1999-10-25 | 2002-09-12 | Byk Gulden Lomberg Chem Fab | Tetrahydrothiopyran derivatives and pharmaceutical compositions containing the same |
| EA005824B1 (ru) * | 2000-06-05 | 2005-06-30 | Алтана Фарма Аг | СОЕДИНЕНИЯ, ЭФФЕКТИВНЫЕ В КАЧЕСТВЕ АГОНИСТОВ β-2-АДРЕНОРЕЦЕПТОРА И ИНГИБИТОРОВ ФОСФОДИЭСТЕРАЗЫ PDE4 |
| PL363391A1 (en) * | 2001-02-15 | 2004-11-15 | Altana Pharma Ag | Phthalayinone-piperidino-derivatives as pde4 inhibitors |
| DE10112864A1 (de) * | 2001-03-16 | 2002-09-19 | Alstom Switzerland Ltd | Verfahren zum Zünden einer thermischen Turbomaschine |
| BR0209149A (pt) * | 2001-04-25 | 2004-07-13 | Altana Pharma Ag | Ftalazinonas |
| NZ529363A (en) * | 2001-04-25 | 2005-08-26 | Altana Pharma Ag | Novel Piperazino-derivatives |
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2003
- 2003-08-06 AU AU2003258576A patent/AU2003258576B2/en not_active Ceased
- 2003-08-06 RS YUP-2005/0112A patent/RS51445B/en unknown
- 2003-08-06 EP EP03792257A patent/EP1537100B1/de not_active Expired - Lifetime
- 2003-08-06 DE DE60313472T patent/DE60313472T2/de not_active Expired - Lifetime
- 2003-08-06 US US10/523,412 patent/US7220746B2/en not_active Expired - Fee Related
- 2003-08-06 ES ES03792257T patent/ES2286491T3/es not_active Expired - Lifetime
- 2003-08-06 KR KR1020057001920A patent/KR101131684B1/ko not_active IP Right Cessation
- 2003-08-06 WO PCT/EP2003/008724 patent/WO2004017974A1/en not_active Application Discontinuation
- 2003-08-06 EP EP03792267A patent/EP1556049A1/de not_active Withdrawn
- 2003-08-06 JP JP2004530086A patent/JP4555684B2/ja not_active Expired - Fee Related
- 2003-08-06 AU AU2003260376A patent/AU2003260376A1/en not_active Abandoned
- 2003-08-06 PL PL373645A patent/PL214701B1/pl unknown
- 2003-08-06 PL PL03372926A patent/PL372926A1/xx not_active Application Discontinuation
- 2003-08-06 AT AT03792257T patent/ATE360627T1/de active
- 2003-08-06 BR BR0313330-3A patent/BR0313330A/pt not_active Application Discontinuation
- 2003-08-06 JP JP2004530096A patent/JP2005538140A/ja active Pending
- 2003-08-06 MX MXPA05001354A patent/MXPA05001354A/es active IP Right Grant
- 2003-08-06 CA CA2494613A patent/CA2494613C/en not_active Expired - Fee Related
- 2003-08-06 WO PCT/EP2003/008675 patent/WO2004018457A1/en active IP Right Grant
- 2003-08-06 CA CA002494634A patent/CA2494634A1/en not_active Abandoned
- 2003-08-06 US US10/523,111 patent/US20060094710A1/en not_active Abandoned
- 2003-08-06 CN CNA038185202A patent/CN1671695A/zh active Pending
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2005
- 2005-01-13 IL IL166271A patent/IL166271A/en not_active IP Right Cessation
- 2005-02-28 IS IS7718A patent/IS2416B/is unknown
- 2005-03-01 HR HR20050198A patent/HRP20050198A2/hr not_active Application Discontinuation
- 2005-03-01 IS IS7721A patent/IS7721A/is unknown
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