JP2005507365A5 - - Google Patents
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- Publication number
- JP2005507365A5 JP2005507365A5 JP2002573735A JP2002573735A JP2005507365A5 JP 2005507365 A5 JP2005507365 A5 JP 2005507365A5 JP 2002573735 A JP2002573735 A JP 2002573735A JP 2002573735 A JP2002573735 A JP 2002573735A JP 2005507365 A5 JP2005507365 A5 JP 2005507365A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbon atoms
- halogen
- substituted
- alkoxy
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 162
- -1 cyano, hydroxy Chemical group 0.000 claims description 127
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 119
- 229910052736 halogen Inorganic materials 0.000 claims description 103
- 150000002367 halogens Chemical class 0.000 claims description 93
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 73
- 125000004043 oxo group Chemical group O=* 0.000 claims description 54
- 125000004429 atoms Chemical group 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 238000006467 substitution reaction Methods 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000002837 carbocyclic group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 125000004434 sulfur atoms Chemical group 0.000 claims description 18
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 15
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 14
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005842 heteroatoms Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 230000001149 cognitive Effects 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 3
- 230000003930 cognitive ability Effects 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000037410 cognitive enhancement Effects 0.000 claims 1
- 230000003931 cognitive performance Effects 0.000 claims 1
- 230000002708 enhancing Effects 0.000 claims 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 29
- 241000700159 Rattus Species 0.000 description 12
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 7
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 230000015654 memory Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 206010027175 Memory impairment Diseases 0.000 description 4
- 238000000540 analysis of variance Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 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 description 3
- 206010057668 Cognitive disease Diseases 0.000 description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- CHXUFRRQOZZSNV-UHFFFAOYSA-N 1-methylpiperidine Chemical group [CH2]N1CCCCC1 CHXUFRRQOZZSNV-UHFFFAOYSA-N 0.000 description 2
- 208000000044 Amnesia Diseases 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N Hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MYSNBAJHBYMBNT-UHFFFAOYSA-N N-[(3-cyclopentyloxy-4-methoxy-2H-pyridin-3-yl)methyl]-N-phenylaniline Chemical compound COC1=CC=NCC1(OC1CCCC1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 MYSNBAJHBYMBNT-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical compound 0.000 description 2
- 125000002431 aminoalkoxy group Chemical compound 0.000 description 2
- 210000004027 cells Anatomy 0.000 description 2
- 235000021171 collation Nutrition 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000002609 media Substances 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 230000003936 working memory Effects 0.000 description 2
- DTBHRRDGLARWLZ-UHFFFAOYSA-N 2-Methylbenzyl radical Chemical compound [CH2]C1=CC=CC=C1C DTBHRRDGLARWLZ-UHFFFAOYSA-N 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-Aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229940035674 ANESTHETICS Drugs 0.000 description 1
- 206010001897 Alzheimer's disease Diseases 0.000 description 1
- 208000008787 Cardiovascular Disease Diseases 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 208000008208 Craniocerebral Trauma Diseases 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N Cyclic guanosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 206010048653 Enzyme inhibition Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229940088597 Hormone Drugs 0.000 description 1
- 201000001971 Huntington's disease Diseases 0.000 description 1
- 206010022114 Injury Diseases 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- 208000001652 Memory Disorders Diseases 0.000 description 1
- 206010061536 Parkinson's disease Diseases 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 201000011585 Pick's disease Diseases 0.000 description 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003444 anaesthetic Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000004059 degradation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 201000011240 frontotemporal dementia Diseases 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular Effects 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 230000000051 modifying Effects 0.000 description 1
- 230000000926 neurological Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000002829 reduced Effects 0.000 description 1
- 230000002441 reversible Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26265101P | 2001-01-22 | 2001-01-22 | |
| US26719601P | 2001-02-08 | 2001-02-08 | |
| US30614001P | 2001-07-19 | 2001-07-19 | |
| PCT/US2002/001508 WO2002074726A2 (en) | 2001-01-22 | 2002-01-22 | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005507365A JP2005507365A (ja) | 2005-03-17 |
| JP2005507365A5 true JP2005507365A5 (xx) | 2008-02-21 |
| JP4223287B2 JP4223287B2 (ja) | 2009-02-12 |
Family
ID=27401532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573735A Expired - Fee Related JP4223287B2 (ja) | 2001-01-22 | 2002-01-22 | 新規な化合物及び製薬上許容し得るそれらの塩並びにそれらを用いた薬剤組成物 |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1353907A2 (xx) |
| JP (1) | JP4223287B2 (xx) |
| KR (1) | KR100856622B1 (xx) |
| CN (1) | CN100378075C (xx) |
| AU (1) | AU2002303078B2 (xx) |
| BG (1) | BG108003A (xx) |
| BR (1) | BR0206943A (xx) |
| CA (1) | CA2435847A1 (xx) |
| CL (1) | CL2004001165A1 (xx) |
| CZ (1) | CZ20031986A3 (xx) |
| EE (1) | EE05362B1 (xx) |
| HK (1) | HK1066215A1 (xx) |
| HR (1) | HRP20030662A2 (xx) |
| HU (1) | HUP0302793A3 (xx) |
| IL (1) | IL156958A0 (xx) |
| MA (1) | MA25996A1 (xx) |
| MX (1) | MXPA03006519A (xx) |
| NO (1) | NO329548B1 (xx) |
| NZ (1) | NZ527081A (xx) |
| PL (1) | PL373301A1 (xx) |
| SK (1) | SK9152003A3 (xx) |
| WO (1) | WO2002074726A2 (xx) |
| YU (1) | YU57603A (xx) |
| ZA (1) | ZA200305623B (xx) |
Families Citing this family (32)
| 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 |
| CA2438480C (en) * | 2001-02-14 | 2011-05-03 | Abbott Laboratories | Glucocorticoid receptor modulators |
| RU2354648C2 (ru) | 2002-07-19 | 2009-05-10 | Мемори Фармасьютиклз Корпорейшн | Соединения 6-амино-1н-индазола и 4-аминобензофурана в качестве ингибиторов фосфодиэстеразы 4 |
| JP2006504656A (ja) * | 2002-07-19 | 2006-02-09 | メモリー・ファーマシューティカルズ・コーポレイション | Ｎ−置換されたアニリン及びジフェニルアミンアナログを含むホスホジエステラーゼ４インヒビター |
| KR20050075430A (ko) | 2002-11-19 | 2005-07-20 | 메모리 파마슈티칼스 코포레이션 | 포스포디에스테라제 4 억제제 |
| US20060040981A1 (en) * | 2002-11-22 | 2006-02-23 | Daniel Dube | Use of phosphodiesterase-4 inhibitors as enhancers of cognition |
| PT1578740E (pt) * | 2002-12-27 | 2007-05-31 | Lundbeck & Co As H | Derivados de 1, 2, 4-triaminobenzeno úteis para tratamento de distúrbios do sistema nervoso central |
| FR2856595B1 (fr) * | 2003-06-27 | 2008-05-30 | Exonhit Therapeutics Sa | Methodes et compositions pour le traitement de deficits cognitifs. |
| JP2007504201A (ja) | 2003-09-05 | 2007-03-01 | アルタナ ファルマ アクチエンゲゼルシャフト | 真性糖尿病の治療のためのｐｄｅ４阻害剤の使用 |
| MY141255A (en) * | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
| CA2571133C (en) | 2004-07-15 | 2011-04-19 | Japan Tobacco Inc. | Fused benzamide compound and vanilloid receptor 1 (vr1) activity inhibitor |
| WO2006049968A1 (en) * | 2004-10-28 | 2006-05-11 | Merck & Co., Inc. | Pyrimidine and quinoline potentiators of metabotropic glutamate receptors |
| US8017633B2 (en) | 2005-03-08 | 2011-09-13 | Nycomed Gmbh | Roflumilast for the treatment of diabetes mellitus |
| AU2006257863A1 (en) * | 2005-06-10 | 2006-12-21 | F. Hoffmann-La Roche Ag | Trisubstituted amines as phosphodiesterase 4 inhibitors |
| AR057455A1 (es) * | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
| US7906508B2 (en) | 2005-12-28 | 2011-03-15 | Japan Tobacco Inc. | 3,4-dihydrobenzoxazine compounds and inhibitors of vanilloid receptor subtype 1 (VRI) activity |
| WO2008099210A2 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| EP2110375A1 (en) * | 2008-04-14 | 2009-10-21 | CHIESI FARMACEUTICI S.p.A. | Phosphodiesterase-4 inhibitors belonging to the tertiary amine class |
| US8461389B2 (en) | 2008-04-18 | 2013-06-11 | University College Dublin, National University Of Ireland, Dublin | Psycho-pharmaceuticals |
| JP5542059B2 (ja) * | 2008-10-09 | 2014-07-09 | 国立大学法人 岡山大学 | Ｒｘｒ作動性物質を有効成分とする抗アレルギー剤 |
| MX2019008390A (es) * | 2009-06-12 | 2019-09-09 | Abivax | Compuestos utiles para tratar cancer. |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| CN113004249A (zh) | 2009-06-12 | 2021-06-22 | Abivax公司 | 用于治疗过早衰老和尤其是早衰的化合物 |
| EP2533780B1 (en) | 2010-02-12 | 2017-08-23 | AskAt Inc. | 5-ht4 receptor agonists for the treatment of dementia |
| US9550763B2 (en) | 2012-02-09 | 2017-01-24 | Shionogi & Co., Ltd. | Heterocyclic ring and carbocyclic derivative |
| CN102603676B (zh) * | 2012-02-20 | 2014-02-12 | 徐江平 | 一种能避免呕吐反应的磷酸二酯酶4抑制剂 |
| CN104136021B (zh) * | 2012-03-14 | 2016-04-20 | 中国中化股份有限公司 | 取代二苯胺类化合物作为制备抗肿瘤药物的应用 |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| EP3016656B1 (en) | 2013-07-05 | 2021-09-08 | Abivax | Bicyclic compounds useful for treating diseases caused by retroviruses |
| EP3033082B1 (en) | 2013-08-16 | 2021-06-16 | Universiteit Maastricht | Treatment of cognitive impairment with pde4 inhibitor |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994027971A1 (en) * | 1993-05-27 | 1994-12-08 | Smithkline Beecham Laboratoires Pharmaceutiques | Anti-arrhythmic n-substituted 3-benzazepines or isoquinolines |
| JPH07206789A (ja) * | 1993-09-01 | 1995-08-08 | Taisho Pharmaceut Co Ltd | コンブレタスタチン類縁化合物 |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| FR2729142A1 (fr) * | 1995-01-06 | 1996-07-12 | Smithkline Beecham Lab | Nouvelles amines heterocycliques, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu'agents anti-arythmiques |
| EP0994100B1 (en) * | 1997-06-24 | 2006-08-30 | Nikken Chemicals Company, Limited | 3-anilino-2-cycloalkenone derivates |
| CA2373990C (en) * | 1999-05-21 | 2007-05-08 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| EP1116711B1 (de) * | 1999-12-18 | 2005-12-14 | Wella Aktiengesellschaft | 2-Aminoalkyl-1,4-diaminobenzol-Derivate und diese Verbindungen enthaltende Färbemittel |
-
2002
- 2002-01-22 CN CNB028070100A patent/CN100378075C/zh not_active Expired - Fee Related
- 2002-01-22 KR KR1020037009624A patent/KR100856622B1/ko not_active IP Right Cessation
- 2002-01-22 MX MXPA03006519A patent/MXPA03006519A/es active IP Right Grant
- 2002-01-22 NZ NZ527081A patent/NZ527081A/xx unknown
- 2002-01-22 YU YU57603A patent/YU57603A/sh unknown
- 2002-01-22 SK SK915-2003A patent/SK9152003A3/sk unknown
- 2002-01-22 PL PL02373301A patent/PL373301A1/xx not_active Application Discontinuation
- 2002-01-22 AU AU2002303078A patent/AU2002303078B2/en not_active Ceased
- 2002-01-22 BR BR0206943-1A patent/BR0206943A/pt not_active Application Discontinuation
- 2002-01-22 EE EEP200300347A patent/EE05362B1/xx not_active IP Right Cessation
- 2002-01-22 WO PCT/US2002/001508 patent/WO2002074726A2/en active Application Filing
- 2002-01-22 EP EP02731078A patent/EP1353907A2/en not_active Withdrawn
- 2002-01-22 IL IL15695802A patent/IL156958A0/xx unknown
- 2002-01-22 CA CA002435847A patent/CA2435847A1/en not_active Abandoned
- 2002-01-22 JP JP2002573735A patent/JP4223287B2/ja not_active Expired - Fee Related
- 2002-01-22 CZ CZ20031986A patent/CZ20031986A3/cs unknown
- 2002-01-22 HU HU0302793A patent/HUP0302793A3/hu unknown
-
2003
- 2003-07-18 BG BG108003A patent/BG108003A/bg unknown
- 2003-07-21 NO NO20033288A patent/NO329548B1/no not_active IP Right Cessation
- 2003-07-21 ZA ZA2003/05623A patent/ZA200305623B/en unknown
- 2003-07-22 MA MA27246A patent/MA25996A1/fr unknown
- 2003-08-20 HR HR20030662A patent/HRP20030662A2/hr not_active Application Discontinuation
-
2004
- 2004-05-20 CL CL200401165A patent/CL2004001165A1/es unknown
- 2004-11-17 HK HK04109061A patent/HK1066215A1/xx not_active IP Right Cessation
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