CA2595252A1 - Novel 6-pyridylphenanthridines - Google Patents
Novel 6-pyridylphenanthridines Download PDFInfo
- Publication number
- CA2595252A1 CA2595252A1 CA002595252A CA2595252A CA2595252A1 CA 2595252 A1 CA2595252 A1 CA 2595252A1 CA 002595252 A CA002595252 A CA 002595252A CA 2595252 A CA2595252 A CA 2595252A CA 2595252 A1 CA2595252 A1 CA 2595252A1
- Authority
- CA
- Canada
- Prior art keywords
- alkoxy
- compounds
- alkyl
- substituted
- salts
- 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.)
- Abandoned
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- JTKIQRJYVVHKRH-UHFFFAOYSA-N 6-pyridin-2-ylphenanthridine Chemical class N1=CC=CC=C1C1=NC2=CC=CC=C2C2=CC=CC=C12 JTKIQRJYVVHKRH-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- -1 1-4C-alkyl Chemical group 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 45
- 150000001204 N-oxides Chemical class 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 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
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 229910052740 iodine Inorganic materials 0.000 abstract description 10
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 5
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- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 13
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 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 9
- 230000005764 inhibitory process Effects 0.000 description 9
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- 125000001424 substituent group Chemical group 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- BIVMWDQSMDXTCT-VXGBXAGGSA-N (1r,2r)-2-(3,4-dimethoxyphenyl)cyclohexan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1[C@@H]1[C@H](N)CCCC1 BIVMWDQSMDXTCT-VXGBXAGGSA-N 0.000 description 3
- CKUUWZSXSMTFIO-VXGBXAGGSA-N 1,2-dimethoxy-4-[(1r,2r)-2-nitrocyclohexyl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1[C@@H]1[C@H]([N+]([O-])=O)CCCC1 CKUUWZSXSMTFIO-VXGBXAGGSA-N 0.000 description 3
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Gynecology & Obstetrics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05100690.6 | 2005-02-01 | ||
| EP05100690 | 2005-02-01 | ||
| PCT/EP2006/050557 WO2006082185A1 (en) | 2005-02-01 | 2006-01-31 | Novel 6-pyridylphenanthridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2595252A1 true CA2595252A1 (en) | 2006-08-10 |
Family
ID=34938616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002595252A Abandoned CA2595252A1 (en) | 2005-02-01 | 2006-01-31 | Novel 6-pyridylphenanthridines |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080119505A1 (enExample) |
| EP (1) | EP1846390B1 (enExample) |
| JP (1) | JP2008528556A (enExample) |
| AT (1) | ATE461189T1 (enExample) |
| AU (1) | AU2006210231A1 (enExample) |
| CA (1) | CA2595252A1 (enExample) |
| DE (1) | DE602006012938D1 (enExample) |
| EA (1) | EA200701626A1 (enExample) |
| ES (1) | ES2342728T3 (enExample) |
| WO (1) | WO2006082185A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| MXPA06009892A (es) * | 2004-03-10 | 2007-03-01 | Altana Pharma Ag | Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4). |
| WO2009109525A1 (en) * | 2008-03-03 | 2009-09-11 | Nycomed Gmbh | Use of a specific pde4 inhibitor for the treatment and/or prophylaxis of non-alcoholic fatty liver disease |
| US8987461B2 (en) | 2012-12-06 | 2015-03-24 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| CN108658778A (zh) * | 2018-06-19 | 2018-10-16 | 上海华堇生物技术有限责任公司 | 一种3,4-二甲氧基-β-硝基苯乙烯的新制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2250569C (en) | 1996-03-26 | 2005-05-10 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel phenanthridines substituted in the 6 position |
| PL2589599T4 (pl) | 2004-03-03 | 2015-06-30 | Takeda Gmbh | Nowe hydroksy-6-heteroarylofenantrydyny i ich zastosowanie jako inhibitorów PDE4 |
-
2006
- 2006-01-31 WO PCT/EP2006/050557 patent/WO2006082185A1/en not_active Ceased
- 2006-01-31 JP JP2007552659A patent/JP2008528556A/ja not_active Withdrawn
- 2006-01-31 EP EP06707926A patent/EP1846390B1/en not_active Expired - Lifetime
- 2006-01-31 AT AT06707926T patent/ATE461189T1/de not_active IP Right Cessation
- 2006-01-31 CA CA002595252A patent/CA2595252A1/en not_active Abandoned
- 2006-01-31 ES ES06707926T patent/ES2342728T3/es not_active Expired - Lifetime
- 2006-01-31 DE DE602006012938T patent/DE602006012938D1/de not_active Expired - Lifetime
- 2006-01-31 EA EA200701626A patent/EA200701626A1/ru unknown
- 2006-01-31 US US11/795,981 patent/US20080119505A1/en not_active Abandoned
- 2006-01-31 AU AU2006210231A patent/AU2006210231A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006210231A1 (en) | 2006-08-10 |
| JP2008528556A (ja) | 2008-07-31 |
| ATE461189T1 (de) | 2010-04-15 |
| DE602006012938D1 (de) | 2010-04-29 |
| US20080119505A1 (en) | 2008-05-22 |
| EP1846390B1 (en) | 2010-03-17 |
| ES2342728T3 (es) | 2010-07-13 |
| WO2006082185A1 (en) | 2006-08-10 |
| EA200701626A1 (ru) | 2008-06-30 |
| EP1846390A1 (en) | 2007-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130131 |