AU2005220034A1 - Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors - Google Patents
Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors Download PDFInfo
- Publication number
- AU2005220034A1 AU2005220034A1 AU2005220034A AU2005220034A AU2005220034A1 AU 2005220034 A1 AU2005220034 A1 AU 2005220034A1 AU 2005220034 A AU2005220034 A AU 2005220034A AU 2005220034 A AU2005220034 A AU 2005220034A AU 2005220034 A1 AU2005220034 A1 AU 2005220034A1
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- Australia
- Prior art keywords
- hydrogen
- alkyl
- alkoxy
- compounds
- methoxy
- Prior art date
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 5
- 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 description 3
- 150000001875 compounds Chemical class 0.000 claims description 323
- -1 2,2-difluoroethoxy Chemical group 0.000 claims description 200
- 229910052739 hydrogen Inorganic materials 0.000 claims description 165
- 239000001257 hydrogen Substances 0.000 claims description 165
- 150000002431 hydrogen Chemical class 0.000 claims description 100
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 47
- 150000001204 N-oxides Chemical class 0.000 claims description 43
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 36
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 239000001301 oxygen Chemical group 0.000 claims description 26
- 229910052717 sulfur Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000011593 sulfur Chemical group 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
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- 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 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229940080818 propionamide Drugs 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 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 7
- HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 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 1
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Classifications
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Otolaryngology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04100959 | 2004-03-09 | ||
| EP04100959.8 | 2004-03-09 | ||
| EP05100545 | 2005-01-27 | ||
| EP05100545.2 | 2005-01-27 | ||
| PCT/EP2005/051025 WO2005084104A2 (en) | 2004-03-09 | 2005-03-08 | Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005220034A1 true AU2005220034A1 (en) | 2005-09-15 |
Family
ID=34921314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005220034A Abandoned AU2005220034A1 (en) | 2004-03-09 | 2005-03-08 | Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20070191414A1 (https=) |
| EP (1) | EP1745025A2 (https=) |
| JP (1) | JP2007527899A (https=) |
| KR (1) | KR20060124784A (https=) |
| AU (1) | AU2005220034A1 (https=) |
| BR (1) | BRPI0508361A (https=) |
| CA (1) | CA2558375A1 (https=) |
| IL (1) | IL177497A0 (https=) |
| NO (1) | NO20064417L (https=) |
| WO (1) | WO2005084104A2 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2495827C (en) * | 2002-08-29 | 2012-05-08 | 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. |
| AU2005212857B2 (en) | 2004-02-18 | 2011-04-28 | Takeda Gmbh | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (PDE) 4 inhibitors |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| CN104803974A (zh) | 2004-03-03 | 2015-07-29 | 塔科达有限责任公司 | 新的羟基-6-杂芳基菲啶及其作为pde4抑制剂的用途 |
| JP2007527901A (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 | アミド置換された新規のヒドロキシ−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 |
| ES2337083T3 (es) | 2005-03-02 | 2010-04-20 | Nycomed Gmbh | (2r,4ar,10br)-6-(2,6-dimetoxipiridin-3-il)-9-exoti-8-metoxi-1,2,3,4,4a,10b-hexahidrofenantridin-2-ol, sal de hc1. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA48216C2 (uk) * | 1996-01-31 | 2002-08-15 | Бік Гулден Ломберг Кеміше Фабрік Гмбх | Фенантридини та лікарський засіб для лікування захворювань дихальних шляхів |
| US6127378A (en) * | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| WO1997035854A1 (de) * | 1996-03-26 | 1997-10-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Neue in 6-position substituierte phenanthridine |
| DE69822162T2 (de) * | 1997-07-25 | 2005-01-27 | Altana Pharma Ag | Neue tetrazolderivate |
| JP2001510827A (ja) * | 1997-07-25 | 2001-08-07 | 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 | 置換６−フェニルフェナントリジン |
| DK1075477T3 (da) * | 1998-05-05 | 2003-06-30 | Altana Pharma Ag | Nye benzonaphthyridin-N-oxider |
| EP1650193A3 (en) * | 1999-01-15 | 2006-10-04 | ALTANA Pharma AG | 6-Phenylphenanthridines with PDE-IV inhibiting activity |
| CA2495827C (en) * | 2002-08-29 | 2012-05-08 | 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. |
-
2005
- 2005-03-08 JP JP2007502338A patent/JP2007527899A/ja not_active Withdrawn
- 2005-03-08 EP EP05729761A patent/EP1745025A2/en not_active Withdrawn
- 2005-03-08 KR KR1020067020594A patent/KR20060124784A/ko not_active Withdrawn
- 2005-03-08 BR BRPI0508361-3A patent/BRPI0508361A/pt not_active IP Right Cessation
- 2005-03-08 AU AU2005220034A patent/AU2005220034A1/en not_active Abandoned
- 2005-03-08 CA CA002558375A patent/CA2558375A1/en not_active Abandoned
- 2005-03-08 WO PCT/EP2005/051025 patent/WO2005084104A2/en not_active Ceased
- 2005-03-08 US US10/591,478 patent/US20070191414A1/en not_active Abandoned
-
2006
- 2006-08-15 IL IL177497A patent/IL177497A0/en unknown
- 2006-09-29 NO NO20064417A patent/NO20064417L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005084104A2 (en) | 2005-09-15 |
| US20070191414A1 (en) | 2007-08-16 |
| CA2558375A1 (en) | 2005-09-15 |
| JP2007527899A (ja) | 2007-10-04 |
| IL177497A0 (en) | 2006-12-10 |
| EP1745025A2 (en) | 2007-01-24 |
| NO20064417L (no) | 2006-10-10 |
| BRPI0508361A (pt) | 2007-11-20 |
| KR20060124784A (ko) | 2006-12-05 |
| WO2005084104A3 (en) | 2005-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: NYCOMED GMBH Free format text: FORMER NAME: ALTANA PHARMA AG |
|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |