TW200540157A - Novel heterocyclyl-substituted hydroxy-6-phenylphenanthridines - Google Patents
Novel heterocyclyl-substituted hydroxy-6-phenylphenanthridines Download PDFInfo
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- TW200540157A TW200540157A TW094106491A TW94106491A TW200540157A TW 200540157 A TW200540157 A TW 200540157A TW 094106491 A TW094106491 A TW 094106491A TW 94106491 A TW94106491 A TW 94106491A TW 200540157 A TW200540157 A TW 200540157A
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- Prior art keywords
- alkyl
- hydrogen
- group
- substituted
- methoxy
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- ZCOWHHNEZZCOJZ-UHFFFAOYSA-N 6-phenylphenanthridin-1-ol Chemical class C=12C=CC=CC2=C2C(O)=CC=CC2=NC=1C1=CC=CC=C1 ZCOWHHNEZZCOJZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 352
- -1 2,2-difluoroethoxy Chemical group 0.000 claims description 264
- 239000001257 hydrogen Substances 0.000 claims description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims description 156
- 150000002431 hydrogen Chemical class 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 78
- 150000003839 salts Chemical class 0.000 claims description 62
- 229910052731 fluorine Inorganic materials 0.000 claims description 58
- 239000011737 fluorine Substances 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000001204 N-oxides Chemical class 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 239000011593 sulfur Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 22
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 7
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 235000013336 milk Nutrition 0.000 claims description 3
- 239000008267 milk Substances 0.000 claims description 3
- 210000004080 milk Anatomy 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 3
- ZBFYBQQGOWYYDI-UHFFFAOYSA-N 1,2,3,4,4a,5-hexahydrophenanthridin-2-ol Chemical compound N1C=C2C=CC=CC2=C2C1CCC(O)C2 ZBFYBQQGOWYYDI-UHFFFAOYSA-N 0.000 claims description 2
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 125000005630 sialyl group Chemical group 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 208000018569 Respiratory Tract disease Diseases 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 7
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 abstract description 7
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 202
- 229960000583 acetic acid Drugs 0.000 description 68
- 239000007858 starting material Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 8
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- IUHSKHLYJAVALM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-nitrocyclohexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1C([N+]([O-])=O)CCC(=O)C1 IUHSKHLYJAVALM-UHFFFAOYSA-N 0.000 description 6
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
-
- 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
-
- 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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04005005 | 2004-03-03 | ||
| EP04106372 | 2004-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200540157A true TW200540157A (en) | 2005-12-16 |
Family
ID=34961674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094106491A TW200540157A (en) | 2004-03-03 | 2005-03-03 | Novel heterocyclyl-substituted hydroxy-6-phenylphenanthridines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20070191413A1 (enExample) |
| EP (1) | EP1812400A1 (enExample) |
| JP (1) | JP2007526284A (enExample) |
| KR (1) | KR20060130684A (enExample) |
| AR (1) | AR049419A1 (enExample) |
| AU (1) | AU2005223370A1 (enExample) |
| BR (1) | BRPI0508256A (enExample) |
| CA (1) | CA2557730A1 (enExample) |
| IL (1) | IL177301A0 (enExample) |
| NO (1) | NO20064220L (enExample) |
| NZ (1) | NZ549109A (enExample) |
| TW (1) | TW200540157A (enExample) |
| WO (1) | WO2005090311A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2281658T3 (es) | 2002-08-29 | 2007-10-01 | Nycomed Gmbh | 3-hidroxi-6-fenilfenantridinas como inhibidores de pde-4. |
| WO2004019944A1 (en) * | 2002-08-29 | 2004-03-11 | Altana Pharma Ag | 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| EP1720835B1 (en) | 2004-02-18 | 2012-12-12 | Nycomed GmbH | Novel guanidinyl-substituted hydroxy-6-phenylphenanthridines as effective phosphodiesterase (pde) 4 inhibitors |
| HRP20130828T1 (en) | 2004-03-03 | 2013-09-30 | Takeda Gmbh | Novel hydroxy-6-heroarylphenanthridines and their use as pde4 inhibitors |
| EP1725534A1 (en) * | 2004-03-10 | 2006-11-29 | Altana Pharma AG | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| NZ560268A (en) | 2005-03-02 | 2010-12-24 | Nycomed Gmbh | Novel salts of 6-heterocyclyl substituted hexahydrophenanthridine derivatives |
| JP5362729B2 (ja) | 2007-10-04 | 2013-12-11 | エフ．ホフマン−ラ ロシュ アーゲー | シクロプロピルアリールアミド誘導体及びその使用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0533280B2 (en) * | 1991-09-20 | 2004-12-01 | Glaxo Group Limited | Novel medical use for tachykinin antagonists |
| EA001205B1 (ru) * | 1996-01-31 | 2000-12-25 | Бык Гульден Ломберг Хемише Фабрик Гмбх | Новые фенантридины |
| US6127378A (en) * | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| ATE234300T1 (de) * | 1996-11-11 | 2003-03-15 | Altana Pharma Ag | Benzonaphthyridine als bronchialtherapeutika |
| WO1999005113A1 (en) * | 1997-07-25 | 1999-02-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted 6-phenylphenanthridines |
| CA2297923A1 (en) * | 1997-07-25 | 1999-02-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel tetrazole-substituted 6-phenyl-pheanathridines as pde inhibitors |
| DE69808099T2 (de) * | 1997-07-25 | 2003-05-15 | Altana Pharma Ag | Substituierte 6-alkylphenanthridine |
| DE59904535D1 (de) * | 1998-05-05 | 2003-04-17 | Altana Pharma Ag | Neue Benzonaphtyridin-N-oxide |
| SI1147087T1 (en) * | 1999-01-15 | 2005-10-31 | Altana Pharma Ag | Phenanthridine-n-oxides with pde-iv inhibiting activity |
| BR0007527B1 (pt) * | 1999-01-15 | 2011-12-27 | fenilfenantridinas com atividade inibitària de pde-iv, seu uso, bem como medicamento compreendendo as mesmas. | |
| ATE294793T1 (de) * | 1999-01-15 | 2005-05-15 | Altana Pharma Ag | Phenantrhridin-n-oxides mit pde-iv hemmender wirkung |
| AU2001283935B2 (en) * | 2000-07-14 | 2006-07-13 | Altana Pharma Ag | Novel 6-heteroarylphenanthridines |
| PT1377574E (pt) * | 2001-02-21 | 2005-05-31 | Byk Gulden Lomberg Chem Fab | 6-fenilbenzonaftiridinas |
| WO2004018431A2 (en) * | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Novel phenanthridines |
| WO2004019944A1 (en) * | 2002-08-29 | 2004-03-11 | Altana Pharma Ag | 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| ES2281658T3 (es) * | 2002-08-29 | 2007-10-01 | Nycomed Gmbh | 3-hidroxi-6-fenilfenantridinas como inhibidores de pde-4. |
| WO2004031724A2 (en) * | 2002-09-30 | 2004-04-15 | Ciphergen Biosystems, Inc. | Apparatus and method for expression and capture of biomolecules and complexes on adsorbent surfaces |
| EP1720835B1 (en) * | 2004-02-18 | 2012-12-12 | Nycomed GmbH | Novel guanidinyl-substituted hydroxy-6-phenylphenanthridines as effective phosphodiesterase (pde) 4 inhibitors |
| CA2558375A1 (en) * | 2004-03-09 | 2005-09-15 | Altana Pharma Ag | Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| JP2007527900A (ja) * | 2004-03-10 | 2007-10-04 | アルタナ ファルマ アクチエンゲゼルシャフト | チオ含有の新規のヒドロキシ−６−フェニルフェナントリジン及びｐｄｅ４インヒビターとしてのそれらの使用 |
| EP1725534A1 (en) * | 2004-03-10 | 2006-11-29 | Altana Pharma AG | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| AU2005219581A1 (en) * | 2004-03-10 | 2005-09-15 | Nycomed Gmbh | Novel difluoroethoxy-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
| US20080119505A1 (en) * | 2005-02-01 | 2008-05-22 | Altana Pharma Ag | Novel 6-Pyridylphenanthridines |
| AU2006219862A1 (en) * | 2005-03-02 | 2006-09-08 | Nycomed Gmbh | 6-Heteroaryl-1,2,3,4,4a, 10b-hexahydro-phenanthridines as PDE-4 inhibitors for the treatment of inflammatory disorders |
| WO2006095009A1 (en) * | 2005-03-09 | 2006-09-14 | Nycomed Gmbh | Amido-substituted 6-phenylphenanthridines |
| US20080015160A1 (en) * | 2005-11-04 | 2008-01-17 | Johji Inazawa | Method for detecting cancer and a method for suppressing cancer |
-
2005
- 2005-03-02 AR ARP050100781A patent/AR049419A1/es unknown
- 2005-03-03 JP JP2007501292A patent/JP2007526284A/ja not_active Withdrawn
- 2005-03-03 AU AU2005223370A patent/AU2005223370A1/en not_active Abandoned
- 2005-03-03 TW TW094106491A patent/TW200540157A/zh unknown
- 2005-03-03 EP EP05716896A patent/EP1812400A1/en not_active Withdrawn
- 2005-03-03 BR BRPI0508256-0A patent/BRPI0508256A/pt not_active IP Right Cessation
- 2005-03-03 CA CA002557730A patent/CA2557730A1/en not_active Abandoned
- 2005-03-03 WO PCT/EP2005/050946 patent/WO2005090311A1/en not_active Ceased
- 2005-03-03 NZ NZ549109A patent/NZ549109A/en unknown
- 2005-03-03 US US10/590,805 patent/US20070191413A1/en not_active Abandoned
- 2005-03-03 KR KR1020067019918A patent/KR20060130684A/ko not_active Ceased
-
2006
- 2006-08-06 IL IL177301A patent/IL177301A0/en unknown
- 2006-09-18 NO NO20064220A patent/NO20064220L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20064220L (no) | 2006-09-18 |
| AU2005223370A1 (en) | 2005-09-29 |
| IL177301A0 (en) | 2006-12-10 |
| BRPI0508256A (pt) | 2007-07-31 |
| WO2005090311A8 (en) | 2006-10-26 |
| US20070191413A1 (en) | 2007-08-16 |
| EP1812400A1 (en) | 2007-08-01 |
| WO2005090311A1 (en) | 2005-09-29 |
| CA2557730A1 (en) | 2005-09-29 |
| NZ549109A (en) | 2010-05-28 |
| JP2007526284A (ja) | 2007-09-13 |
| AR049419A1 (es) | 2006-08-02 |
| KR20060130684A (ko) | 2006-12-19 |
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