TW200540159A - Novel thio-containing hydroxy-6-phenylphenanthridines - Google Patents
Novel thio-containing hydroxy-6-phenylphenanthridines Download PDFInfo
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- TW200540159A TW200540159A TW094107371A TW94107371A TW200540159A TW 200540159 A TW200540159 A TW 200540159A TW 094107371 A TW094107371 A TW 094107371A TW 94107371 A TW94107371 A TW 94107371A TW 200540159 A TW200540159 A TW 200540159A
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- Prior art keywords
- hydrogen
- alkyl
- methoxy
- alkoxy
- phenyl
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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 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 373
- -1 2,2-difluoroethoxy Chemical group 0.000 claims abstract description 200
- 239000001257 hydrogen Substances 0.000 claims abstract description 193
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 193
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 116
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 52
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052717 sulfur Chemical group 0.000 claims abstract description 9
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 39
- 238000000034 method Methods 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 239000011737 fluorine Substances 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 19
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
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- 238000011282 treatment Methods 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 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 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
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- 239000000126 substance Substances 0.000 claims description 7
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
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- 230000001404 mediated effect Effects 0.000 claims description 3
- 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 description 3
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- DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 claims 1
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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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- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims 1
- YKIROZABKINQNX-UHFFFAOYSA-N 4-methyl-1h-1,2-benzodiazepine Chemical compound N1N=CC(C)=CC2=CC=CC=C21 YKIROZABKINQNX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D221/12—Phenanthridines
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Landscapes
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04100988 | 2004-03-10 | ||
| EP05100692 | 2005-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200540159A true TW200540159A (en) | 2005-12-16 |
Family
ID=34961402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094107371A TW200540159A (en) | 2004-03-10 | 2005-03-10 | Novel thio-containing hydroxy-6-phenylphenanthridines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080161339A1 (https=) |
| EP (1) | EP1725533A1 (https=) |
| JP (1) | JP2007527900A (https=) |
| KR (1) | KR20060124783A (https=) |
| AR (1) | AR048001A1 (https=) |
| AU (1) | AU2005221831A1 (https=) |
| BR (1) | BRPI0508473A (https=) |
| CA (1) | CA2558390A1 (https=) |
| IL (1) | IL177499A0 (https=) |
| NO (1) | NO20064416L (https=) |
| TW (1) | TW200540159A (https=) |
| WO (1) | WO2005087744A1 (https=) |
Families Citing this family (13)
| 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. |
| AU2005212857B2 (en) | 2004-02-18 | 2011-04-28 | Takeda Gmbh | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (PDE) 4 inhibitors |
| 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 |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| 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. |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| CN101522682A (zh) | 2006-10-30 | 2009-09-02 | 诺瓦提斯公司 | 作为抗炎剂的杂环化合物 |
| MX2010003155A (es) | 2007-10-04 | 2010-04-01 | Hoffmann La Roche | Derivados de ciclopropil aril amida y uso de los mismos. |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
Family Cites Families (8)
| 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 |
-
2005
- 2005-03-09 CA CA002558390A patent/CA2558390A1/en not_active Abandoned
- 2005-03-09 JP JP2007502342A patent/JP2007527900A/ja not_active Withdrawn
- 2005-03-09 WO PCT/EP2005/051052 patent/WO2005087744A1/en not_active Ceased
- 2005-03-09 KR KR1020067020591A patent/KR20060124783A/ko not_active Withdrawn
- 2005-03-09 AU AU2005221831A patent/AU2005221831A1/en not_active Abandoned
- 2005-03-09 EP EP05716969A patent/EP1725533A1/en not_active Withdrawn
- 2005-03-09 BR BRPI0508473-3A patent/BRPI0508473A/pt not_active IP Right Cessation
- 2005-03-09 US US10/591,768 patent/US20080161339A1/en not_active Abandoned
- 2005-03-10 AR ARP050100916A patent/AR048001A1/es unknown
- 2005-03-10 TW TW094107371A patent/TW200540159A/zh unknown
-
2006
- 2006-08-15 IL IL177499A patent/IL177499A0/en unknown
- 2006-09-29 NO NO20064416A patent/NO20064416L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080161339A1 (en) | 2008-07-03 |
| EP1725533A1 (en) | 2006-11-29 |
| AR048001A1 (es) | 2006-03-15 |
| CA2558390A1 (en) | 2005-09-22 |
| NO20064416L (no) | 2006-12-07 |
| WO2005087744A1 (en) | 2005-09-22 |
| JP2007527900A (ja) | 2007-10-04 |
| BRPI0508473A (pt) | 2007-07-31 |
| IL177499A0 (en) | 2006-12-10 |
| KR20060124783A (ko) | 2006-12-05 |
| AU2005221831A1 (en) | 2005-09-22 |
| WO2005087744A8 (en) | 2006-10-26 |
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