MXPA06009892A - Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4). - Google Patents
Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4).Info
- Publication number
- MXPA06009892A MXPA06009892A MXPA06009892A MXPA06009892A MXPA06009892A MX PA06009892 A MXPA06009892 A MX PA06009892A MX PA06009892 A MXPA06009892 A MX PA06009892A MX PA06009892 A MXPA06009892 A MX PA06009892A MX PA06009892 A MXPA06009892 A MX PA06009892A
- Authority
- MX
- Mexico
- Prior art keywords
- hydrogen
- alkyl
- methoxy
- hexahydro
- compounds
- Prior art date
Links
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title abstract description 4
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 4
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 378
- -1 2,2-difluoroethoxy Chemical group 0.000 claims abstract description 342
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 285
- 239000001257 hydrogen Substances 0.000 claims abstract description 285
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 174
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 184
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 141
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 132
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 150000001204 N-oxides Chemical class 0.000 claims description 102
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 150000003839 salts Chemical class 0.000 claims description 88
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 60
- 239000001301 oxygen Substances 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 58
- 229910052717 sulfur Inorganic materials 0.000 claims description 58
- 239000011593 sulfur Substances 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004076 pyridyl group Chemical group 0.000 claims description 46
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 41
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 41
- 125000002757 morpholinyl group Chemical group 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 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 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 125000002950 monocyclic group Chemical group 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 29
- VXVVBHZWCMDJPJ-KAYWLYCHSA-N n-[(3r,4r)-4-[[4-(2-hydroxy-5-piperidin-1-ylbenzoyl)benzoyl]amino]azepan-3-yl]pyridine-4-carboxamide Chemical compound N([C@@H]1CNCCC[C@H]1NC(=O)C1=CC=C(C=C1)C(=O)C1=CC(=CC=C1O)N1CCCCC1)C(=O)C1=CC=NC=C1 VXVVBHZWCMDJPJ-KAYWLYCHSA-N 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 101100070530 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) het-6 gene Proteins 0.000 claims description 21
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
- YSNIPFQCRHRGSO-UHFFFAOYSA-N 5-[[6-chloro-5-[4-(2-hydroxyphenyl)phenyl]-1H-benzimidazol-2-yl]oxy]-N-hydroxy-2-methylbenzamide Chemical compound ClC=1C(=CC2=C(NC(=N2)OC=2C=CC(=C(C(=O)NO)C=2)C)C=1)C1=CC=C(C=C1)C1=C(C=CC=C1)O YSNIPFQCRHRGSO-UHFFFAOYSA-N 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 11
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical group C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000004792 2.2-difluoroethoxy group Chemical group FC(CO*)F 0.000 claims description 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- NVFYVOYKTAOECP-QRFRQXIXSA-N 4-[(2s,4as,10bs)-9-(difluoromethoxy)-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-cyclopropylbenzamide Chemical compound C=1([C@@H]2C[C@@H](O)CC[C@@H]2N=2)C=C(OC(F)F)C(OC)=CC=1C=2C(C=C1)=CC=C1C(=O)NC1CC1 NVFYVOYKTAOECP-QRFRQXIXSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- TYBPDSCQEYBLEB-GZGNHOFSSA-N 3-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=CC(C(=O)N(C(C)C)C(C)C)=C1 TYBPDSCQEYBLEB-GZGNHOFSSA-N 0.000 claims description 2
- XVKSYVWQNHHKQV-KJXAQDMKSA-N 3-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-cyclobutylbenzamide Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=1)=CC=CC=1C(=O)NC1CCC1 XVKSYVWQNHHKQV-KJXAQDMKSA-N 0.000 claims description 2
- XUIVMRIGLWWQOM-UHFFFAOYSA-N 4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)-n,n-dimethylbenzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2C2CC(O)CCC2N=C1C1=CC=C(C(=O)N(C)C)C=C1 XUIVMRIGLWWQOM-UHFFFAOYSA-N 0.000 claims description 2
- IWPVRJOVAGOWOW-UHFFFAOYSA-N 4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)-n-(2-pyridin-2-ylethyl)benzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2C2CC(O)CCC2N=C1C(C=C1)=CC=C1C(=O)NCCC1=CC=CC=N1 IWPVRJOVAGOWOW-UHFFFAOYSA-N 0.000 claims description 2
- RCIFXRMESZRVKK-UHFFFAOYSA-N 4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2C2CC(O)CCC2N=C1C(C=C1)=CC=C1C(=O)NCCC1=CC=NC=C1 RCIFXRMESZRVKK-UHFFFAOYSA-N 0.000 claims description 2
- KFVCBHFHQZURCC-SYYKKAFVSA-N 4-[(2r,4ar,10br)-2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-(2,6-dimethoxypyridin-3-yl)benzamide Chemical compound COC1=NC(OC)=CC=C1NC(=O)C1=CC=C(C=2C3=CC(OC)=C(OC)C=C3[C@H]3C[C@H](O)CC[C@H]3N=2)C=C1 KFVCBHFHQZURCC-SYYKKAFVSA-N 0.000 claims description 2
- OPVBRSGHFDVMEI-SYYKKAFVSA-N 4-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-cyclopropylbenzamide Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC1CC1 OPVBRSGHFDVMEI-SYYKKAFVSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- BHIMLCFDJDWNJF-UHFFFAOYSA-N n-cyclopropyl-4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)benzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2C2CC(O)CCC2N=C1C(C=C1)=CC=C1C(=O)NC1CC1 BHIMLCFDJDWNJF-UHFFFAOYSA-N 0.000 claims description 2
- NVFYVOYKTAOECP-UHFFFAOYSA-N n-cyclopropyl-4-[9-(difluoromethoxy)-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]benzamide Chemical compound N=1C2CCC(O)CC2C=2C=C(OC(F)F)C(OC)=CC=2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NVFYVOYKTAOECP-UHFFFAOYSA-N 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- JZYDHQRZQOEWIN-UHFFFAOYSA-N 4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)-n-(4-methylpiperazin-1-yl)benzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2C2CC(O)CCC2N=C1C(C=C1)=CC=C1C(=O)NN1CCN(C)CC1 JZYDHQRZQOEWIN-UHFFFAOYSA-N 0.000 claims 1
- QCDPHPRVFCZICY-UHFFFAOYSA-N 4-(2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl)-n-quinolin-3-ylbenzamide Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC=C(C=C3)C3=NC4CCC(O)CC4C=4C=C(C(=CC=43)OC)OC)=CN=C21 QCDPHPRVFCZICY-UHFFFAOYSA-N 0.000 claims 1
- DEZXVIXQPOAVBT-KJXAQDMKSA-N 4-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-cyclobutylbenzamide Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC1CCC1 DEZXVIXQPOAVBT-KJXAQDMKSA-N 0.000 claims 1
- KFVCBHFHQZURCC-VCOUNFBDSA-N 4-[(2s,4as,10bs)-2-hydroxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-n-(2,6-dimethoxypyridin-3-yl)benzamide Chemical compound COC1=NC(OC)=CC=C1NC(=O)C1=CC=C(C=2C3=CC(OC)=C(OC)C=C3[C@@H]3C[C@@H](O)CC[C@@H]3N=2)C=C1 KFVCBHFHQZURCC-VCOUNFBDSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 1
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 1
- 229960005286 carbaryl Drugs 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
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Classifications
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04100990 | 2004-03-10 | ||
| EP04106677 | 2004-12-17 | ||
| PCT/EP2005/051054 WO2005087745A1 (en) | 2004-03-10 | 2005-03-09 | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06009892A true MXPA06009892A (es) | 2007-03-01 |
Family
ID=34965034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06009892A MXPA06009892A (es) | 2004-03-10 | 2005-03-09 | Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4). |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20070185149A1 (enExample) |
| EP (1) | EP1725534A1 (enExample) |
| JP (1) | JP2007527901A (enExample) |
| KR (1) | KR20060130697A (enExample) |
| CN (1) | CN1926113B (enExample) |
| AR (1) | AR049324A1 (enExample) |
| AU (1) | AU2005221832A1 (enExample) |
| BR (1) | BRPI0508481A (enExample) |
| CA (1) | CA2558391A1 (enExample) |
| IL (1) | IL177496A0 (enExample) |
| MX (1) | MXPA06009892A (enExample) |
| NO (1) | NO20064415L (enExample) |
| NZ (1) | NZ549254A (enExample) |
| TW (1) | TW200600499A (enExample) |
| WO (1) | WO2005087745A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004019945A1 (en) | 2002-08-29 | 2004-03-11 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| EP1539164B1 (en) | 2002-08-29 | 2006-12-20 | ALTANA Pharma AG | 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| GB0316915D0 (en) | 2003-07-18 | 2003-08-20 | Glaxo Group Ltd | Compounds |
| WO2005077906A1 (en) | 2004-02-18 | 2005-08-25 | Altana Pharma Ag | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (pde) 4 inhibitors |
| AU2005219576B2 (en) | 2004-03-03 | 2011-06-30 | Takeda Gmbh | Novel hydroxy-6-heteroarylphenanthridines and their use as PDE4 inhibitors |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| WO2006027344A2 (en) | 2004-09-08 | 2006-03-16 | Altana Pharma Ag | 3-oxa-10-aza-phenanthrenes as pde4 or pde3/4 inhibitors |
| WO2006027345A2 (en) | 2004-09-08 | 2006-03-16 | Altana Pharma Ag | Novel 3-thia-10-aza-phenanthrene derivatives |
| NZ589278A (en) | 2005-03-02 | 2012-04-27 | Nycomed Gmbh | Selected salts of 6-heterocyclyl substituted hexahydrophenanthridine derivatives |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| WO2008052734A1 (en) | 2006-10-30 | 2008-05-08 | Novartis Ag | Heterocyclic compounds as antiinflammatory agents |
| KR101178674B1 (ko) | 2007-10-04 | 2012-08-30 | 에프. 호프만-라 로슈 아게 | 사이클로프로필 아릴 아마이드 유도체 및 이의 용도 |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| JP2012519723A (ja) | 2009-03-09 | 2012-08-30 | ビーエーエスエフ ソシエタス・ヨーロピア | 置換型２−ニトロビフェニル類の調製方法 |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| CA2828219A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Pyrazolo [1,5-a] pyridines as trk inhibitors |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT533280E (pt) * | 1991-09-20 | 2001-01-31 | Glaxo Group Ltd | Novas utilizacoes medicas para antagonistas de taquiquinina |
| ATE233735T1 (de) * | 1996-01-31 | 2003-03-15 | Altana Pharma Ag | Neue phenanthridine |
| US6127378A (en) * | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| DK0937074T3 (da) * | 1996-11-11 | 2003-06-23 | Altana Pharma Ag | Benzonaphthyridiner som bronkiale terapeutiske midler |
| PT1000034E (pt) * | 1997-07-25 | 2003-02-28 | Altana Pharma Ag | 6-alquilfenantridinas substituidas |
| WO1999005113A1 (en) * | 1997-07-25 | 1999-02-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted 6-phenylphenanthridines |
| ATE260899T1 (de) * | 1997-07-25 | 2004-03-15 | Altana Pharma Ag | Neue tetrazolderivate |
| US6306869B1 (en) * | 1998-05-05 | 2001-10-23 | Byk Gulden Lomberg Chemische Febrik Gmbh | N-oxides |
| TR200101938T2 (tr) * | 1999-01-15 | 2001-12-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pde-ıv inhibe edici aktivitesi olan fenilfenantridinler. |
| PT1147087E (pt) * | 1999-01-15 | 2005-09-30 | Altana Pharma Ag | Feantridina-n-oxidos com actividade de inibicao de pde-iv |
| WO2000042034A1 (en) * | 1999-01-15 | 2000-07-20 | Byk Gulden | Phenanthridine-n-oxides with pde-iv inhibiting activity |
| ES2236288T3 (es) * | 2000-07-14 | 2005-07-16 | Altana Pharma Ag | 6-heteroarilfenantridinas. |
| US6936622B2 (en) * | 2001-02-21 | 2005-08-30 | Altana Pharma Ag | 6-phenylbenzonaphthyridines |
| WO2004018431A2 (en) * | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Novel phenanthridines |
| EP1539164B1 (en) * | 2002-08-29 | 2006-12-20 | ALTANA Pharma AG | 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| WO2004019945A1 (en) * | 2002-08-29 | 2004-03-11 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| AU2003277069A1 (en) * | 2002-09-30 | 2004-04-23 | Ciphergen Biosystems, Inc. | Apparatus and method for expression and capture of biomolecules and complexes on adsorbent surfaces |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| US20070191414A1 (en) * | 2004-03-09 | 2007-08-16 | Altana Pharma Ag | Novel isoamido-substituted hydroxy-6-phenylphenanthridines |
| US20070259909A1 (en) * | 2004-03-10 | 2007-11-08 | Altana Pharma Ag | Novel Difluoroethoxy-Substituted Hydroxy-6-Phenylphenanthridines and Their Use as Pde4 Inhibitors |
| AU2005221831A1 (en) * | 2004-03-10 | 2005-09-22 | Nycomed Gmbh | Novel thio-containing hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
| EP1846390B1 (en) * | 2005-02-01 | 2010-03-17 | Nycomed GmbH | Novel 6-pyridylphenanthridines |
| WO2006092417A1 (en) * | 2005-03-02 | 2006-09-08 | Nycomed Gmbh | 6 -heteroaryl-1, 2, 3,4,4a, 1ob-hexahydro-phenanthridines as pde-4 inhibitors for the treatment of inflammatory disorders |
| NZ589278A (en) * | 2005-03-02 | 2012-04-27 | Nycomed Gmbh | Selected salts of 6-heterocyclyl substituted hexahydrophenanthridine derivatives |
| JP2008532980A (ja) * | 2005-03-09 | 2008-08-21 | 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 | アミド置換された６−フェニルフェナントリジン |
-
2005
- 2005-03-09 CN CN2005800068554A patent/CN1926113B/zh not_active Expired - Fee Related
- 2005-03-09 AU AU2005221832A patent/AU2005221832A1/en not_active Abandoned
- 2005-03-09 MX MXPA06009892A patent/MXPA06009892A/es not_active Application Discontinuation
- 2005-03-09 CA CA002558391A patent/CA2558391A1/en not_active Abandoned
- 2005-03-09 EP EP05740073A patent/EP1725534A1/en not_active Withdrawn
- 2005-03-09 KR KR1020067020318A patent/KR20060130697A/ko not_active Ceased
- 2005-03-09 BR BRPI0508481-4A patent/BRPI0508481A/pt not_active IP Right Cessation
- 2005-03-09 JP JP2007502343A patent/JP2007527901A/ja not_active Withdrawn
- 2005-03-09 WO PCT/EP2005/051054 patent/WO2005087745A1/en not_active Ceased
- 2005-03-09 NZ NZ549254A patent/NZ549254A/en unknown
- 2005-03-09 US US10/591,480 patent/US20070185149A1/en not_active Abandoned
- 2005-03-10 TW TW094107344A patent/TW200600499A/zh unknown
- 2005-03-11 AR ARP050100931A patent/AR049324A1/es unknown
-
2006
- 2006-08-15 IL IL177496A patent/IL177496A0/en unknown
- 2006-09-29 NO NO20064415A patent/NO20064415L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20070185149A1 (en) | 2007-08-09 |
| CN1926113B (zh) | 2010-06-23 |
| AU2005221832A1 (en) | 2005-09-22 |
| WO2005087745A8 (en) | 2006-10-26 |
| WO2005087745A1 (en) | 2005-09-22 |
| NZ549254A (en) | 2010-06-25 |
| BRPI0508481A (pt) | 2007-07-31 |
| IL177496A0 (en) | 2006-12-10 |
| NO20064415L (no) | 2006-10-10 |
| AR049324A1 (es) | 2006-07-19 |
| TW200600499A (en) | 2006-01-01 |
| EP1725534A1 (en) | 2006-11-29 |
| CN1926113A (zh) | 2007-03-07 |
| KR20060130697A (ko) | 2006-12-19 |
| JP2007527901A (ja) | 2007-10-04 |
| CA2558391A1 (en) | 2005-09-22 |
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| Publication | Publication Date | Title |
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| AU2003253408A1 (en) | Novel phenanthridines | |
| MXPA06009892A (es) | Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4). | |
| HK1208865A1 (en) | Novel hydroxy-6-heteroarylphenanthridines and their use as pde4 inhibitors | |
| AU2005212857B2 (en) | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (PDE) 4 inhibitors | |
| US20070191414A1 (en) | Novel isoamido-substituted hydroxy-6-phenylphenanthridines | |
| US20070191413A1 (en) | Novel heterocycle-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors | |
| JP2008532980A (ja) | アミド置換された６−フェニルフェナントリジン | |
| MXPA06009893A (en) | Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors | |
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| HK1102587A (en) | Novel thio-containing hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors | |
| HK1166063A (en) | Novel hydroxy-6-heteroarylphenanthridines and their use as pde4 inhibitors | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC | Change of company name or juridical status |
Owner name: ABBOTT GMBH & CO. KG |
|
| FA | Abandonment or withdrawal |