JP2007527899A5 - - Google Patents
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- Publication number
- JP2007527899A5 JP2007527899A5 JP2007502338A JP2007502338A JP2007527899A5 JP 2007527899 A5 JP2007527899 A5 JP 2007527899A5 JP 2007502338 A JP2007502338 A JP 2007502338A JP 2007502338 A JP2007502338 A JP 2007502338A JP 2007527899 A5 JP2007527899 A5 JP 2007527899A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- alkyl
- alkoxy
- substituted
- ethoxy
- 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- Withdrawn
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 58
- 239000001257 hydrogen Substances 0.000 claims 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 31
- -1 2,2-difluoroethoxy Chemical group 0.000 claims 25
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims 12
- 150000001204 N-oxides Chemical class 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000001301 oxygen Chemical group 0.000 claims 9
- 229910052717 sulfur Chemical group 0.000 claims 9
- 239000011593 sulfur Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- CEABVLPXHAQPPU-UHFFFAOYSA-N C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(N)=C1 Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(N)=C1 CEABVLPXHAQPPU-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 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 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 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 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- HYVWIZBUHDYWGY-UHFFFAOYSA-N 2-(dimethylamino)-n-[3-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]butanamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(NC(=O)C(CC)N(C)C)=C1 HYVWIZBUHDYWGY-UHFFFAOYSA-N 0.000 claims 1
- YICUAMQTWNFMMF-UHFFFAOYSA-N 3-(carbamoylamino)-n-[3-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]propanamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(NC(=O)CCNC(N)=O)=C1 YICUAMQTWNFMMF-UHFFFAOYSA-N 0.000 claims 1
- BTXGYNTYEYOGMV-UHFFFAOYSA-N CCOC(C(OC)=C1)=CC2=C1C(C(C=C1)=CC=C1N)=NC(CC1)C2CC1O.OC(C1CC1)=O Chemical compound CCOC(C(OC)=C1)=CC2=C1C(C(C=C1)=CC=C1N)=NC(CC1)C2CC1O.OC(C1CC1)=O BTXGYNTYEYOGMV-UHFFFAOYSA-N 0.000 claims 1
- CMZGSSOQYWWEBL-UHFFFAOYSA-N CN1CCC(C(O)=O)CC1.C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C(C=1)=CC=CC=1NC(=O)CCN1CCCCC1 Chemical compound CN1CCC(C(O)=O)CC1.C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C(C=1)=CC=CC=1NC(=O)CCN1CCCCC1 CMZGSSOQYWWEBL-UHFFFAOYSA-N 0.000 claims 1
- OTWFNFMGAQJGRV-UHFFFAOYSA-N N-[4-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-N',N'-dimethylbutanediamide 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1.C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=C(NC(=O)CCC(=O)N(C)C)C=C1 OTWFNFMGAQJGRV-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- UOOVGXQHAKYGJF-UHFFFAOYSA-N cyclopropanecarboxylic acid N-[4-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-3-methoxypropanamide Chemical compound OC(=O)C1CC1.C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=C(NC(=O)CCOC)C=C1 UOOVGXQHAKYGJF-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- FWXYMUQQKREYMH-UHFFFAOYSA-N n-[3-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-2-methoxyacetamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(NC(=O)COC)=C1 FWXYMUQQKREYMH-UHFFFAOYSA-N 0.000 claims 1
- IZKVULTYCSJCOE-UHFFFAOYSA-N n-[3-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-3-methoxypropanamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(NC(=O)CCOC)=C1 IZKVULTYCSJCOE-UHFFFAOYSA-N 0.000 claims 1
- GTBKUYBWFLTYIB-UHFFFAOYSA-N n-[3-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-n',n'-dimethylbutanediamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=CC(NC(=O)CCC(=O)N(C)C)=C1 GTBKUYBWFLTYIB-UHFFFAOYSA-N 0.000 claims 1
- CVKMJAWIHLMWJC-UHFFFAOYSA-N n-[4-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-2-methoxyacetamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C1=CC=C(NC(=O)COC)C=C1 CVKMJAWIHLMWJC-UHFFFAOYSA-N 0.000 claims 1
- KEOZCQIFYIILCB-UHFFFAOYSA-N n-[4-(9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)phenyl]-3-piperidin-1-ylpropanamide Chemical compound C1=2C=C(OC)C(OCC)=CC=2C2CC(O)CCC2N=C1C(C=C1)=CC=C1NC(=O)CCN1CCCCC1 KEOZCQIFYIILCB-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04100959 | 2004-03-09 | ||
| EP05100545 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2007527899A JP2007527899A (ja) | 2007-10-04 |
| JP2007527899A5 true JP2007527899A5 (https=) | 2008-04-24 |
Family
ID=34921314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007502338A Withdrawn JP2007527899A (ja) | 2004-03-09 | 2005-03-08 | 新規のイソアミド置換されたヒドロキシ−６−フェニルフェナントリジン |
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 |
|---|---|---|---|---|
| JP4587294B2 (ja) * | 2002-08-29 | 2010-11-24 | 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 | Ｐｄｅ４インヒビターとしての２−ヒドロキシ−６−フェニルフェナントリジン |
| ATE353217T1 (de) * | 2002-08-29 | 2007-02-15 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridine als pde-4 inhibitoren |
| CA2556086C (en) | 2004-02-18 | 2014-04-01 | Altana Pharma Ag | 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 |
| PL2589599T4 (pl) * | 2004-03-03 | 2015-06-30 | Takeda Gmbh | Nowe hydroksy-6-heteroarylofenantrydyny i ich zastosowanie jako inhibitorów PDE4 |
| EP1725534A1 (en) * | 2004-03-10 | 2006-11-29 | Altana Pharma AG | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| PL1856093T3 (pl) * | 2005-03-02 | 2010-05-31 | Takeda Gmbh | Chlorowodorek (2R,4aR,10bR)-6-(2,6-dimetoksy-pirydyn-3-ylo)-9-etoksy-8-metoksy-1,2,3,4,4a,10b-heksahydrofenantrydyn-2-olu |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9707233A (pt) * | 1996-01-31 | 1999-07-20 | Byk Gulden Lomberg Chem Fab | Fenantridinas |
| US6127378A (en) * | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| SI0889886T1 (en) * | 1996-03-26 | 2003-02-28 | Altana Pharma Ag | Novel phenanthridines substituted in the 6 position |
| PT998460E (pt) * | 1997-07-25 | 2004-07-30 | Altana Pharma Ag | Novos derivados de tetrazole |
| 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 |
| TR200501553T2 (tr) * | 1999-01-15 | 2005-06-21 | Altana Pharma Ag | PDE-IV inhibe edici aktivitesi olan fenilfenantridinler |
| JP4587294B2 (ja) * | 2002-08-29 | 2010-11-24 | 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 | Ｐｄｅ４インヒビターとしての２−ヒドロキシ−６−フェニルフェナントリジン |
| ATE353217T1 (de) * | 2002-08-29 | 2007-02-15 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridine als pde-4 inhibitoren |
-
2005
- 2005-03-08 AU AU2005220034A patent/AU2005220034A1/en not_active Abandoned
- 2005-03-08 EP EP05729761A patent/EP1745025A2/en not_active Withdrawn
- 2005-03-08 JP JP2007502338A patent/JP2007527899A/ja not_active Withdrawn
- 2005-03-08 BR BRPI0508361-3A patent/BRPI0508361A/pt not_active IP Right Cessation
- 2005-03-08 KR KR1020067020594A patent/KR20060124784A/ko not_active Withdrawn
- 2005-03-08 US US10/591,478 patent/US20070191414A1/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
-
2006
- 2006-08-15 IL IL177497A patent/IL177497A0/en unknown
- 2006-09-29 NO NO20064417A patent/NO20064417L/no not_active Application Discontinuation
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