JP2006508987A5 - - Google Patents
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- JP2006508987A5 JP2006508987A5 JP2004553941A JP2004553941A JP2006508987A5 JP 2006508987 A5 JP2006508987 A5 JP 2006508987A5 JP 2004553941 A JP2004553941 A JP 2004553941A JP 2004553941 A JP2004553941 A JP 2004553941A JP 2006508987 A5 JP2006508987 A5 JP 2006508987A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- carbon atoms
- halogen
- cyano
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 433
- -1 cyano, hydroxy Chemical group 0.000 claims 351
- 125000004432 carbon atom Chemical group C* 0.000 claims 333
- 229910052736 halogen Inorganic materials 0.000 claims 303
- 150000002367 halogens Chemical class 0.000 claims 259
- 125000003545 alkoxy group Chemical group 0.000 claims 205
- 125000004093 cyano group Chemical group *C#N 0.000 claims 184
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 161
- 125000003118 aryl group Chemical group 0.000 claims 153
- 125000004043 oxo group Chemical group O=* 0.000 claims 137
- 150000001875 compounds Chemical class 0.000 claims 125
- 125000000623 heterocyclic group Chemical group 0.000 claims 102
- 125000006413 ring segment Chemical group 0.000 claims 102
- 229920006395 saturated elastomer Polymers 0.000 claims 94
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 91
- 125000000753 cycloalkyl group Chemical group 0.000 claims 82
- 229910052760 oxygen Inorganic materials 0.000 claims 56
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 54
- 125000003710 aryl alkyl group Chemical group 0.000 claims 53
- 125000004663 dialkyl amino group Chemical group 0.000 claims 52
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 50
- 125000004414 alkyl thio group Chemical group 0.000 claims 49
- 125000004434 sulfur atom Chemical group 0.000 claims 47
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 46
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 46
- 125000004430 oxygen atom Chemical group O* 0.000 claims 46
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 44
- 125000003282 alkyl amino group Chemical group 0.000 claims 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 43
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 42
- 125000002252 acyl group Chemical group 0.000 claims 42
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 42
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 42
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 42
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 42
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 41
- 239000002253 acid Substances 0.000 claims 41
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 41
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 37
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 36
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 35
- 125000004103 aminoalkyl group Chemical group 0.000 claims 34
- 125000001072 heteroaryl group Chemical group 0.000 claims 29
- 239000005711 Benzoic acid Substances 0.000 claims 23
- 235000010233 benzoic acid Nutrition 0.000 claims 23
- 125000002837 carbocyclic group Chemical group 0.000 claims 21
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 21
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 19
- 239000000203 mixture Substances 0.000 claims 15
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 14
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 13
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 9
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims 9
- 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 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 229920001577 copolymer Chemical class 0.000 claims 7
- 150000003254 radicals Chemical class 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 206010027175 memory impairment Diseases 0.000 claims 5
- HFZZTHJMXZSGFP-UHFFFAOYSA-N 1-benzofuran-2-amine Chemical compound C1=CC=C2OC(N)=CC2=C1 HFZZTHJMXZSGFP-UHFFFAOYSA-N 0.000 claims 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000001089 Multiple system atrophy Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000007954 hypoxia Effects 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 230000009758 senescence Effects 0.000 claims 2
- 208000020431 spinal cord injury Diseases 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 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 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- 229940035674 anesthetics Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 208000025307 bipolar depression Diseases 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000006384 methylpyridyl group Chemical group 0.000 claims 1
- 208000008013 morphine dependence Diseases 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001806 thionaphthenyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 0 CC(C)(C)*NC Chemical compound CC(C)(C)*NC 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42722102P | 2002-11-19 | 2002-11-19 | |
| PCT/US2003/036986 WO2004046113A2 (en) | 2002-11-19 | 2003-11-19 | Pyridine n-oxide compounds as phosphodiesterase 4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006508987A JP2006508987A (ja) | 2006-03-16 |
| JP2006508987A5 true JP2006508987A5 (cg-RX-API-DMAC7.html) | 2007-02-15 |
Family
ID=32326501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004553941A Ceased JP2006508987A (ja) | 2002-11-19 | 2003-11-19 | ホスホジエステラーゼ４阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US7087625B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1569908B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2006508987A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20050075430A (cg-RX-API-DMAC7.html) |
| CN (1) | CN100513397C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE481387T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003295656B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0315705A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2506297A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60334243D1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA05005345A (cg-RX-API-DMAC7.html) |
| NO (1) | NO20052976L (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ540138A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2356893C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004046113A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200503995B (cg-RX-API-DMAC7.html) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7153871B2 (en) * | 2001-01-22 | 2006-12-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs |
| US20030149052A1 (en) * | 2002-01-22 | 2003-08-07 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| AU2003256616B2 (en) * | 2002-07-19 | 2009-08-27 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including N-substituted aniline and diphenylamine analogs |
| DE60325984D1 (de) * | 2002-07-19 | 2009-03-12 | Memory Pharmaceutical Corp | 4-aminobenzofuranverbindungen als phosphodiesterase-4-inhibitoren |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| AU2003282726B2 (en) * | 2002-10-03 | 2010-10-07 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US20090048255A1 (en) * | 2003-07-21 | 2009-02-19 | Schumacher Richard A | Phosphodiesterase 4 inhibitors, including n-substituted aniline and diphenylamine analogs |
| MY141255A (en) * | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
| EP2543376A1 (en) | 2004-04-08 | 2013-01-09 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US7652051B2 (en) | 2004-08-25 | 2010-01-26 | Targegen, Inc. | Heterocyclic compounds and methods of use |
| JP2008543781A (ja) * | 2005-06-10 | 2008-12-04 | メモリー・ファーマシューティカルズ・コーポレイション | ホスフオジエステラーゼ４阻害剤 |
| EP2116523B1 (en) * | 2007-02-27 | 2015-05-06 | National University Corporation Okayama University | Rexinoid compound having alkoxy group |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| KR20100014565A (ko) * | 2007-04-11 | 2010-02-10 | 알콘 리서치, 리미티드 | 알레르기성 비염 및 알레르기성 결막염을 치료하기 위한 ｔｎｆａ의 억제제 및 항히스타민의 용도 |
| US20090182035A1 (en) * | 2007-04-11 | 2009-07-16 | Alcon Research, Ltd. | Use of a combination of olopatadine and cilomilast to treat non-infectious rhinitis and allergic conjunctivitis |
| WO2009067607A2 (en) * | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
| EP2070913A1 (en) | 2007-12-14 | 2009-06-17 | CHIESI FARMACEUTICI S.p.A. | Ester derivatives as phosphodiesterase inhibitors |
| EP2110375A1 (en) * | 2008-04-14 | 2009-10-21 | CHIESI FARMACEUTICI S.p.A. | Phosphodiesterase-4 inhibitors belonging to the tertiary amine class |
| US20100029689A1 (en) * | 2008-07-02 | 2010-02-04 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
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-
2003
- 2003-11-19 CA CA002506297A patent/CA2506297A1/en not_active Abandoned
- 2003-11-19 JP JP2004553941A patent/JP2006508987A/ja not_active Ceased
- 2003-11-19 KR KR1020057008915A patent/KR20050075430A/ko not_active Ceased
- 2003-11-19 AT AT03786857T patent/ATE481387T1/de not_active IP Right Cessation
- 2003-11-19 AU AU2003295656A patent/AU2003295656B2/en not_active Expired - Fee Related
- 2003-11-19 DE DE60334243T patent/DE60334243D1/de not_active Expired - Lifetime
- 2003-11-19 CN CNB2003801036392A patent/CN100513397C/zh not_active Expired - Fee Related
- 2003-11-19 BR BR0315705-9A patent/BR0315705A/pt not_active Application Discontinuation
- 2003-11-19 NZ NZ540138A patent/NZ540138A/en not_active IP Right Cessation
- 2003-11-19 MX MXPA05005345A patent/MXPA05005345A/es active IP Right Grant
- 2003-11-19 EP EP03786857A patent/EP1569908B1/en not_active Expired - Lifetime
- 2003-11-19 WO PCT/US2003/036986 patent/WO2004046113A2/en not_active Ceased
- 2003-11-19 RU RU2005119627/04A patent/RU2356893C2/ru not_active IP Right Cessation
- 2003-11-19 US US10/715,819 patent/US7087625B2/en not_active Expired - Fee Related
-
2005
- 2005-05-18 ZA ZA200503995A patent/ZA200503995B/en unknown
- 2005-06-17 NO NO20052976A patent/NO20052976L/no unknown
-
2006
- 2006-03-20 US US11/378,615 patent/US7700631B2/en not_active Expired - Fee Related
-
2010
- 2010-03-16 US US12/724,750 patent/US20100173942A1/en not_active Abandoned
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