DE602005005638T2 - 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-on-derivate als pde4-inhibitoren - Google Patents
2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-on-derivate als pde4-inhibitoren Download PDFInfo
- Publication number
- DE602005005638T2 DE602005005638T2 DE602005005638T DE602005005638T DE602005005638T2 DE 602005005638 T2 DE602005005638 T2 DE 602005005638T2 DE 602005005638 T DE602005005638 T DE 602005005638T DE 602005005638 T DE602005005638 T DE 602005005638T DE 602005005638 T2 DE602005005638 T2 DE 602005005638T2
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- Germany
- Prior art keywords
- alkyl
- hydrogen
- alkoxy
- formula
- methyl
- Prior art date
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- Expired - Lifetime
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title abstract description 6
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 6
- RUYMSNJFRBMDAM-UHFFFAOYSA-N 2-piperidin-4-yl-4,5-dihydropyridazin-3-one Chemical class O=C1CCC=NN1C1CCNCC1 RUYMSNJFRBMDAM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- -1 1-piperazinyl Chemical group 0.000 claims description 225
- 239000001257 hydrogen Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 150000002431 hydrogen Chemical group 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 54
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 30
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 28
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 27
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 26
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000003003 spiro group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 10
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- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
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- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052717 sulfur Inorganic materials 0.000 claims description 5
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- JQOZLHTULXLTHM-UHFFFAOYSA-N 2-[2-[4-[3-(3,4-dimethoxyphenyl)-5,5-dimethyl-6-oxo-4h-pyridazin-1-yl]piperidin-1-yl]-2-oxoethyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(C(=O)CN2C(C3=CC=CC=C3C2=O)=O)CC1 JQOZLHTULXLTHM-UHFFFAOYSA-N 0.000 claims description 2
- HOXFDOBGBNIKPX-UHFFFAOYSA-N 2-[4-[3-(3,4-dimethoxyphenyl)-5,5-dimethyl-6-oxo-4h-pyridazin-1-yl]piperidin-1-yl]sulfonylbenzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C(=CC=CC=2)C#N)CC1 HOXFDOBGBNIKPX-UHFFFAOYSA-N 0.000 claims description 2
- MKGSHVUYZBZSFZ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-1-[1-(2-methoxybenzoyl)piperidin-4-yl]-5,5-dimethyl-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(C(=O)C=2C(=CC=CC=2)OC)CC1 MKGSHVUYZBZSFZ-UHFFFAOYSA-N 0.000 claims description 2
- QTRTVNQVLHRZDS-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-diethyl-1-[1-(2-methoxybenzoyl)piperidin-4-yl]-4h-pyridazin-6-one Chemical compound O=C1C(CC)(CC)CC(C=2C=C(OC)C(OC)=CC=2)=NN1C(CC1)CCN1C(=O)C1=CC=CC=C1OC QTRTVNQVLHRZDS-UHFFFAOYSA-N 0.000 claims description 2
- NXKMKQNQJSICGX-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-1-[1-(2-methylphenyl)sulfonylpiperidin-4-yl]-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C(=CC=CC=2)C)CC1 NXKMKQNQJSICGX-UHFFFAOYSA-N 0.000 claims description 2
- HURWJFQCAYJYCV-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-1-[1-(3-methylphenyl)sulfonylpiperidin-4-yl]-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C=C(C)C=CC=2)CC1 HURWJFQCAYJYCV-UHFFFAOYSA-N 0.000 claims description 2
- OGACFTLUBPYWFQ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-1-[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C=CC(C)=CC=2)CC1 OGACFTLUBPYWFQ-UHFFFAOYSA-N 0.000 claims description 2
- KHNYQYVNVCGRGZ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-1-[1-[2-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl]-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)F)CC1 KHNYQYVNVCGRGZ-UHFFFAOYSA-N 0.000 claims description 2
- KBYGVCYYJPCVLU-UHFFFAOYSA-N 4-[3-(3,4-dimethoxyphenyl)-5,5-dimethyl-6-oxo-4h-pyridazin-1-yl]-n,n-dimethylpiperidine-1-sulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)N(C)C)CC1 KBYGVCYYJPCVLU-UHFFFAOYSA-N 0.000 claims description 2
- LLTFKYCFMONYKL-UHFFFAOYSA-N 4-[4-[3-(3,4-dimethoxyphenyl)-5,5-dimethyl-6-oxo-4h-pyridazin-1-yl]piperidin-1-yl]sulfonylbenzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(S(=O)(=O)C=2C=CC(=CC=2)C#N)CC1 LLTFKYCFMONYKL-UHFFFAOYSA-N 0.000 claims description 2
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- MXAJVDHGJCYEKL-UHFFFAOYSA-N morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1 MXAJVDHGJCYEKL-UHFFFAOYSA-N 0.000 claims description 2
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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 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- SIZFVKQNIWECRT-UHFFFAOYSA-N 1-(1-benzoylpiperidin-4-yl)-3-(3,4-dimethoxyphenyl)-5,5-diethyl-4h-pyridazin-6-one Chemical compound O=C1C(CC)(CC)CC(C=2C=C(OC)C(OC)=CC=2)=NN1C(CC1)CCN1C(=O)C1=CC=CC=C1 SIZFVKQNIWECRT-UHFFFAOYSA-N 0.000 claims 1
- XHWDOKAWWQRJRZ-UHFFFAOYSA-N 1-[2-[4-[3-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)-5,5-dimethyl-6-oxo-4h-pyridazin-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C(CC1)CCN1C(=O)CN1C(=O)CCC1=O XHWDOKAWWQRJRZ-UHFFFAOYSA-N 0.000 claims 1
- WFDVODACYSGNSA-UHFFFAOYSA-N 2-[4-[3-(3,4-dimethoxyphenyl)-5,5-diethyl-6-oxo-4h-pyridazin-1-yl]piperidin-1-yl]acetamide Chemical compound O=C1C(CC)(CC)CC(C=2C=C(OC)C(OC)=CC=2)=NN1C1CCN(CC(N)=O)CC1 WFDVODACYSGNSA-UHFFFAOYSA-N 0.000 claims 1
- MIHRVFXCEOZVPG-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-1-[1-(3-morpholin-4-yl-3-oxopropyl)piperidin-4-yl]-4h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)(C)C1=O)=NN1C1CCN(CCC(=O)N2CCOCC2)CC1 MIHRVFXCEOZVPG-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
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- 125000004193 piperazinyl group Chemical group 0.000 claims 1
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- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Otolaryngology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04002420 | 2004-02-04 | ||
| EP04002420 | 2004-02-04 | ||
| PCT/EP2005/050415 WO2005075456A1 (en) | 2004-02-04 | 2005-02-01 | 2-(piperidin-4-yl) -4, 5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602005005638D1 DE602005005638D1 (de) | 2008-05-08 |
| DE602005005638T2 true DE602005005638T2 (de) | 2009-05-14 |
Family
ID=34833569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602005005638T Expired - Lifetime DE602005005638T2 (de) | 2004-02-04 | 2005-02-01 | 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-on-derivate als pde4-inhibitoren |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7494990B2 (https=) |
| EP (1) | EP1716133B1 (https=) |
| JP (1) | JP4778449B2 (https=) |
| AT (1) | ATE390419T1 (https=) |
| AU (1) | AU2005210042B2 (https=) |
| CA (1) | CA2554797C (https=) |
| DE (1) | DE602005005638T2 (https=) |
| ES (1) | ES2304692T3 (https=) |
| WO (1) | WO2005075456A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2686909C (en) * | 2007-05-16 | 2016-07-05 | Nycomed Gmbh | Pyrazolone derivatives as pde4 inhibitors |
| AU2013234404B2 (en) * | 2007-05-16 | 2016-04-28 | Takeda Gmbh | Pyrazolone Derivatives as PDE4 Inhibitors |
| 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. |
| AU2012269133A1 (en) | 2011-06-17 | 2014-01-30 | Takeda Gmbh | Novel phthalazinone-pyrrolopyrimidinecarboxamide derivatives |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB858792A (en) * | 1958-02-10 | 1961-01-18 | Sandoz Ltd | New pyridazine derivatives and processes for their manufacture |
| US5267027A (en) | 1991-04-30 | 1993-11-30 | Sanyo Electric Co., Ltd. | Comb filter-type Y/C separator circuit |
| HUT66969A (en) | 1991-10-09 | 1995-01-30 | Syntex Inc | Benzo- and pyrido-pyridazinone- and pyridazin-thion derivatives, pharmaceutical compositions containing the same and process for the production of thereof |
| DE4134893A1 (de) | 1991-10-23 | 1993-04-29 | Merck Patent Gmbh | Thiadiazinone |
| DE4310699A1 (de) | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Thiadiazinone |
| US5798349A (en) | 1994-03-14 | 1998-08-25 | The General Hospital Corporation | Use of green porphyrins to treat neovasculature in the eye |
| DE19502699A1 (de) | 1995-01-28 | 1996-08-01 | Merck Patent Gmbh | Arylalkyl-thiadiazinone |
| DE19514568A1 (de) * | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Arylalkyl-pyridazinone |
| DE19533975A1 (de) | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| DE19604388A1 (de) | 1996-02-07 | 1997-08-14 | Merck Patent Gmbh | Arylalkyl-diazinone |
| TR199901653T2 (xx) | 1997-01-15 | 1999-10-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Fitalazinonlar. |
| WO1999031071A1 (en) | 1997-12-15 | 1999-06-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
| ATE258930T1 (de) | 1997-12-15 | 2004-02-15 | Altana Pharma Ag | Dihydrobenzifurane |
| JP2002506856A (ja) | 1998-03-14 | 2002-03-05 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | フタラジノンｐｄｅｉｉｉ／ｉｖ阻害剤 |
| AU7654200A (en) | 1999-09-14 | 2001-04-17 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone derivatives as pd3/4 inhibitors |
| IL148807A0 (en) | 1999-10-25 | 2002-09-12 | Byk Gulden Lomberg Chem Fab | Tetrahydrothiopyran derivatives and pharmaceutical compositions containing the same |
| DE60036558D1 (de) | 1999-10-25 | 2007-11-08 | Nycomed Gmbh | Phthalazinon-derivate als pde 4 hemmer |
| NZ522882A (en) | 2000-06-05 | 2004-07-30 | Altana Pharma Bv | Pyridazinone compounds effective as beta-2-adrenoreceptor agonists as well as PDE4-inhibitors |
| EE05386B1 (et) | 2001-02-15 | 2011-02-15 | ALTANA�Pharma�AG | Ftalasinoon-piperidinoderivaadid,ÁnendeÁkasutamineÁjaÁravim |
| NZ529221A (en) * | 2001-04-25 | 2005-04-29 | Altana Pharma Ag | Phthalazinones with PDE-inhibiting properties for treatment of airway disorders and other inflammatory conditions |
| CZ20033205A3 (en) | 2001-04-25 | 2004-03-17 | Altana Pharma Ag | Piperazino-derivatives and their use as pde4 inhibitor |
| DE10150517A1 (de) | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
| WO2004018451A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Pyridazinone-derivatives as pde4 inhibitors |
| AU2003255376A1 (en) * | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
| WO2004018450A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
| CA2494613C (en) | 2002-08-10 | 2011-06-28 | Altana Pharma Ag | Pyrrolidinedione substituted piperidine-phthalazones as pde4 inhibitors |
| WO2004017957A1 (en) | 2002-08-20 | 2004-03-04 | Protemix Corporation Limited | Preventing and/or treating cardiovascular disease and/or associated heart failure |
| WO2005075457A1 (en) | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Phthalazinone-derivatives as pde4 inhibitors |
| WO2005075437A1 (en) | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Pyridazinone derivatives and their use as pde4 inhibitors |
-
2005
- 2005-02-01 EP EP05716609A patent/EP1716133B1/en not_active Expired - Lifetime
- 2005-02-01 AT AT05716609T patent/ATE390419T1/de active
- 2005-02-01 DE DE602005005638T patent/DE602005005638T2/de not_active Expired - Lifetime
- 2005-02-01 JP JP2006551846A patent/JP4778449B2/ja not_active Expired - Fee Related
- 2005-02-01 CA CA2554797A patent/CA2554797C/en not_active Expired - Fee Related
- 2005-02-01 US US10/587,836 patent/US7494990B2/en not_active Expired - Fee Related
- 2005-02-01 WO PCT/EP2005/050415 patent/WO2005075456A1/en not_active Ceased
- 2005-02-01 AU AU2005210042A patent/AU2005210042B2/en not_active Ceased
- 2005-02-01 ES ES05716609T patent/ES2304692T3/es not_active Expired - Lifetime
-
2009
- 2009-01-14 US US12/320,005 patent/US7820669B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005075456A1 (en) | 2005-08-18 |
| US20070179146A1 (en) | 2007-08-02 |
| US7494990B2 (en) | 2009-02-24 |
| WO2005075456A8 (en) | 2006-03-02 |
| JP4778449B2 (ja) | 2011-09-21 |
| EP1716133B1 (en) | 2008-03-26 |
| JP2007520528A (ja) | 2007-07-26 |
| AU2005210042B2 (en) | 2011-04-21 |
| DE602005005638D1 (de) | 2008-05-08 |
| ES2304692T3 (es) | 2008-10-16 |
| CA2554797A1 (en) | 2005-08-18 |
| ATE390419T1 (de) | 2008-04-15 |
| CA2554797C (en) | 2012-09-04 |
| EP1716133A1 (en) | 2006-11-02 |
| US7820669B2 (en) | 2010-10-26 |
| US20090131448A1 (en) | 2009-05-21 |
| AU2005210042A1 (en) | 2005-08-18 |
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| 8364 | No opposition during term of opposition |