JP2001510826A - 置換6−アルキルフェナントリジン - Google Patents
置換6−アルキルフェナントリジンInfo
- Publication number
- JP2001510826A JP2001510826A JP2000504111A JP2000504111A JP2001510826A JP 2001510826 A JP2001510826 A JP 2001510826A JP 2000504111 A JP2000504111 A JP 2000504111A JP 2000504111 A JP2000504111 A JP 2000504111A JP 2001510826 A JP2001510826 A JP 2001510826A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- compound
- formula
- alkoxy
- alkyl
- 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- Withdrawn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
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- 239000003814 drug Substances 0.000 claims abstract description 11
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- 239000001257 hydrogen Substances 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 35
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 210000002345 respiratory system Anatomy 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- -1 1,2,3,4,4a, 10b-hexahydrophenanthridine-6-butyrate Chemical compound 0.000 description 26
- 238000000034 method Methods 0.000 description 18
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- 239000002904 solvent Substances 0.000 description 11
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 5
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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 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000010228 Erectile Dysfunction Diseases 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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-
- 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
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97112794 | 1997-07-25 | ||
| EP97112794.9 | 1997-07-25 | ||
| PCT/EP1998/004476 WO1999005112A1 (en) | 1997-07-25 | 1998-07-18 | Substituted 6-alkylphenanthridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001510826A true JP2001510826A (ja) | 2001-08-07 |
| JP2001510826A5 JP2001510826A5 (https=) | 2006-01-05 |
Family
ID=8227118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000504111A Withdrawn JP2001510826A (ja) | 1997-07-25 | 1998-07-18 | 置換6−アルキルフェナントリジン |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6214839B1 (https=) |
| EP (1) | EP1000034B1 (https=) |
| JP (1) | JP2001510826A (https=) |
| AT (1) | ATE224372T1 (https=) |
| AU (1) | AU9066498A (https=) |
| DE (1) | DE69808099T2 (https=) |
| DK (1) | DK1000034T3 (https=) |
| ES (1) | ES2184318T3 (https=) |
| PT (1) | PT1000034E (https=) |
| SI (1) | SI1000034T1 (https=) |
| WO (1) | WO1999005112A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007526283A (ja) * | 2004-03-03 | 2007-09-13 | アルタナ ファルマ アクチエンゲゼルシャフト | 新規のヒドロキシ−6−ヘテロアリー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 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1212089B1 (en) | 1999-08-21 | 2006-03-22 | ALTANA Pharma AG | Synergistic combination of roflumilast and salmeterol |
| PT1303506E (pt) * | 2000-07-14 | 2005-06-30 | Altana Pharma Ag | 6-heteroarilfenantridinas |
| WO2002005616A1 (en) * | 2000-07-14 | 2002-01-24 | Altana Pharma Ag | Novel 6-phenylphenanthridines |
| 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. |
| MXPA05010373A (es) | 2003-04-01 | 2005-12-05 | Applied Research Systems | Inhibidores de fosfodiesterasas en infertilidad. |
| 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 |
| 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 |
| WO2006026725A2 (en) | 2004-08-31 | 2006-03-09 | C.R. Bard, Inc. | Self-sealing ptfe graft with kink resistance |
| 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. |
| JP2008543376A (ja) * | 2005-06-08 | 2008-12-04 | シー・アール・バード・インコーポレーテッド | 無機生体適合性カルシウム塩を有するグラフト及びステント |
| JP2009501027A (ja) | 2005-06-17 | 2009-01-15 | シー・アール・バード・インコーポレイテツド | 締付後のよじれ耐性を有する血管移植片 |
| WO2007056761A2 (en) | 2005-11-09 | 2007-05-18 | C.R. Bard Inc. | Grafts and stent grafts having a radiopaque marker |
| EP2079575B1 (en) | 2006-10-12 | 2021-06-02 | C.R. Bard, Inc. | Methods for making vascular grafts with multiple channels |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199773B (de) * | 1962-02-23 | 1965-09-02 | Hoffmann La Roche | Verfahren zur Herstellung von 6-Methyl-8, 9-methylendioxy-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrophenanthridin und dessen Salzen |
| US3243438A (en) | 1962-02-23 | 1966-03-29 | Hoffmann La Roche | Octahydro phenanthridine compounds |
| US4309545A (en) * | 1980-07-28 | 1982-01-05 | Pfizer Inc. | Oximino-1-hydroxyoctahydrobenzo[c]quinolines and derivatives thereof |
-
1998
- 1998-07-18 DK DK98942571T patent/DK1000034T3/da active
- 1998-07-18 AU AU90664/98A patent/AU9066498A/en not_active Abandoned
- 1998-07-18 DE DE69808099T patent/DE69808099T2/de not_active Expired - Fee Related
- 1998-07-18 US US09/462,507 patent/US6214839B1/en not_active Expired - Fee Related
- 1998-07-18 EP EP98942571A patent/EP1000034B1/en not_active Expired - Lifetime
- 1998-07-18 AT AT98942571T patent/ATE224372T1/de not_active IP Right Cessation
- 1998-07-18 PT PT98942571T patent/PT1000034E/pt unknown
- 1998-07-18 SI SI9830300T patent/SI1000034T1/xx unknown
- 1998-07-18 WO PCT/EP1998/004476 patent/WO1999005112A1/en not_active Ceased
- 1998-07-18 ES ES98942571T patent/ES2184318T3/es not_active Expired - Lifetime
- 1998-07-18 JP JP2000504111A patent/JP2001510826A/ja not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007526283A (ja) * | 2004-03-03 | 2007-09-13 | アルタナ ファルマ アクチエンゲゼルシャフト | 新規のヒドロキシ−6−ヘテロアリー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 |
| JP2011074094A (ja) * | 2004-03-03 | 2011-04-14 | Nycomed Gmbh | 新規のヒドロキシ−6−ヘテロアリールフェナントリジン及び当該化合物を含有する医薬組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999005112A1 (en) | 1999-02-04 |
| DE69808099D1 (de) | 2002-10-24 |
| ES2184318T3 (es) | 2003-04-01 |
| DK1000034T3 (da) | 2003-01-27 |
| DE69808099T2 (de) | 2003-05-15 |
| AU9066498A (en) | 1999-02-16 |
| EP1000034A1 (en) | 2000-05-17 |
| SI1000034T1 (en) | 2003-04-30 |
| PT1000034E (pt) | 2003-02-28 |
| US6214839B1 (en) | 2001-04-10 |
| ATE224372T1 (de) | 2002-10-15 |
| EP1000034B1 (en) | 2002-09-18 |
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Legal Events
| Date | Code | Title | Description |
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| A524 | Written submission of copy of amendment under article 19 pct |
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| A621 | Written request for application examination |
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