CA2330738A1 - Novel n-oxides of benzonaphthyridines - Google Patents
Novel n-oxides of benzonaphthyridines Download PDFInfo
- Publication number
- CA2330738A1 CA2330738A1 CA002330738A CA2330738A CA2330738A1 CA 2330738 A1 CA2330738 A1 CA 2330738A1 CA 002330738 A CA002330738 A CA 002330738A CA 2330738 A CA2330738 A CA 2330738A CA 2330738 A1 CA2330738 A1 CA 2330738A1
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- Prior art keywords
- compounds
- alkoxy
- alkyl
- formula
- hydrogen
- Prior art date
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- BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical class N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000003814 drug Substances 0.000 claims abstract description 20
- -1 1-piperidyl Chemical group 0.000 claims description 69
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- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
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- 239000007858 starting material Substances 0.000 claims description 5
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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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- NPFVRBCDMFKOPY-UHFFFAOYSA-N 3-(4-imidazol-1-ylthiophen-2-yl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC(N2C=NC=C2)=CS1 NPFVRBCDMFKOPY-UHFFFAOYSA-N 0.000 description 2
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- 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920003199 poly(diethylsiloxane) Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 229940070376 protein Drugs 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000019254 respiratory burst Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000002883 vasorelaxation effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98108124.3 | 1998-05-05 | ||
| EP98108124 | 1998-05-05 | ||
| PCT/EP1999/002827 WO1999057118A1 (de) | 1998-05-05 | 1999-04-27 | Neue n-oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2330738A1 true CA2330738A1 (en) | 1999-11-11 |
Family
ID=8231880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002330738A Abandoned CA2330738A1 (en) | 1998-05-05 | 1999-04-27 | Novel n-oxides of benzonaphthyridines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6306869B1 (enExample) |
| EP (1) | EP1075477B1 (enExample) |
| JP (1) | JP2002513793A (enExample) |
| AT (1) | ATE234301T1 (enExample) |
| AU (1) | AU3928999A (enExample) |
| CA (1) | CA2330738A1 (enExample) |
| DE (1) | DE59904535D1 (enExample) |
| DK (1) | DK1075477T3 (enExample) |
| ES (1) | ES2195571T3 (enExample) |
| PT (1) | PT1075477E (enExample) |
| SI (1) | SI1075477T1 (enExample) |
| WO (1) | WO1999057118A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5970199A (en) | 1998-08-31 | 2000-03-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine-n-oxides comprising a pde3 and pde4 inhibiting activity |
| SI1212089T1 (sl) * | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Sinergisticna kombinacija roflumilasta in salmeterola |
| DE60133879D1 (de) | 2000-01-11 | 2008-06-19 | Nycomed Gmbh | Phenanthridin -n- oxide |
| SI1377574T1 (enExample) * | 2001-02-21 | 2005-08-31 | Altana Pharma Ag | |
| PL373598A1 (en) * | 2002-08-17 | 2005-09-05 | Altana Pharma Ag | Novel benzonaphthyridines |
| AU2003255493B8 (en) * | 2002-08-29 | 2009-03-26 | Takeda Gmbh | 2-hydroxy-6-phenylphenanthridines as PDE-4 inhibitors |
| JP4587295B2 (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３−ヒドロキシ−６−フェニルフェナントリジン |
| DE60313331T2 (de) * | 2002-09-04 | 2008-01-03 | Nycomed Gmbh | Neue benzonaphthyridine |
| US7470704B2 (en) | 2002-09-04 | 2008-12-30 | Nycomed Gmbh | Benzonaphthyridines |
| IS7839A (is) * | 2002-11-22 | 2004-05-23 | Merck Frosst Canada Ltd. | 4-oxó-1-(3-setið fenýl-1,4-díhýdró-1,8-naftýridín-3-karboxamíð fosfódíesterasa-4 hindrar |
| AU2005212857B2 (en) * | 2004-02-18 | 2011-04-28 | Takeda Gmbh | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (PDE) 4 inhibitors |
| SI2589599T1 (sl) | 2004-03-03 | 2014-10-30 | Takeda Gmbh | Novi hidroksi-6-heteroarilfenantridini in njihova uporaba kot PDE4 inhibitorji |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| WO2005084104A2 (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 |
| AU2005219581A1 (en) * | 2004-03-10 | 2005-09-15 | Nycomed Gmbh | Novel difluoroethoxy-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
| AU2005221832A1 (en) * | 2004-03-10 | 2005-09-22 | Nycomed Gmbh | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
| AU2005223386A1 (en) | 2004-03-17 | 2005-09-29 | Nycomed Gmbh | Novel N- (alkoxyalkyl) carbamoyl - substituted 6-phenyl-benzonaphthyridine derivatives and their use as PDE3/4 inhibitors |
| EP1791847A2 (en) | 2004-09-08 | 2007-06-06 | Altana Pharma AG | Novel 3-thia-10-aza-phenanthrene derivatives |
| ES2365926T3 (es) * | 2004-09-08 | 2011-10-13 | Nycomed Gmbh | 3-oxa-10-aza-fenantrenos como inhibidores de pde4 o pde3/4. |
| NZ560268A (en) | 2005-03-02 | 2010-12-24 | Nycomed Gmbh | Novel salts of 6-heterocyclyl substituted hexahydrophenanthridine derivatives |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| WO2007134136A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0247971A3 (en) * | 1986-05-29 | 1990-01-17 | Sandoz Ag | Novel pharmaceutical compositions comprising and use of cis-6-(4-acetanilido)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin |
| NZ334976A (en) | 1996-11-11 | 2000-10-27 | Byk Gulden Lomberg Chem Fab | Benzonaphthyridine derivatives and their use for treating airway disorders and dermatoses |
-
1999
- 1999-04-27 ES ES99922133T patent/ES2195571T3/es not_active Expired - Lifetime
- 1999-04-27 JP JP2000547088A patent/JP2002513793A/ja not_active Withdrawn
- 1999-04-27 WO PCT/EP1999/002827 patent/WO1999057118A1/de not_active Ceased
- 1999-04-27 DK DK99922133T patent/DK1075477T3/da active
- 1999-04-27 AU AU39289/99A patent/AU3928999A/en not_active Abandoned
- 1999-04-27 EP EP99922133A patent/EP1075477B1/de not_active Expired - Lifetime
- 1999-04-27 AT AT99922133T patent/ATE234301T1/de not_active IP Right Cessation
- 1999-04-27 PT PT99922133T patent/PT1075477E/pt unknown
- 1999-04-27 SI SI9930279T patent/SI1075477T1/xx unknown
- 1999-04-27 CA CA002330738A patent/CA2330738A1/en not_active Abandoned
- 1999-04-27 DE DE59904535T patent/DE59904535D1/de not_active Expired - Fee Related
- 1999-04-27 US US09/673,649 patent/US6306869B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1075477E (pt) | 2003-07-31 |
| JP2002513793A (ja) | 2002-05-14 |
| EP1075477A1 (de) | 2001-02-14 |
| AU3928999A (en) | 1999-11-23 |
| US6306869B1 (en) | 2001-10-23 |
| DK1075477T3 (da) | 2003-06-30 |
| EP1075477B1 (de) | 2003-03-12 |
| SI1075477T1 (en) | 2003-08-31 |
| ATE234301T1 (de) | 2003-03-15 |
| DE59904535D1 (de) | 2003-04-17 |
| WO1999057118A1 (de) | 1999-11-11 |
| ES2195571T3 (es) | 2003-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |