JP2008519824A5 - - Google Patents
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- Publication number
- JP2008519824A5 JP2008519824A5 JP2007540782A JP2007540782A JP2008519824A5 JP 2008519824 A5 JP2008519824 A5 JP 2008519824A5 JP 2007540782 A JP2007540782 A JP 2007540782A JP 2007540782 A JP2007540782 A JP 2007540782A JP 2008519824 A5 JP2008519824 A5 JP 2008519824A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- aryl
- heterocyclyl
- halogen
- 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.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims description 189
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 174
- 125000003118 aryl group Chemical group 0.000 claims description 173
- 125000000623 heterocyclic group Chemical group 0.000 claims description 172
- 229910052736 halogen Inorganic materials 0.000 claims description 139
- 150000002367 halogens Chemical class 0.000 claims description 119
- 125000001072 heteroaryl group Chemical group 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
- 239000001257 hydrogen Substances 0.000 claims description 114
- 150000002431 hydrogen Chemical class 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 87
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000003282 alkyl amino group Chemical group 0.000 claims description 62
- -1 heterocyclylsulfonyl Chemical group 0.000 claims description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 36
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
- 239000000651 prodrug Substances 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 22
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 21
- 125000004043 oxo group Chemical group O=* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims description 20
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 18
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 18
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
- 125000005001 aminoaryl group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 18
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 150000003456 sulfonamides Chemical class 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000006315 carbonylation Effects 0.000 claims description 4
- 238000005810 carbonylation reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 72
- 238000000034 method Methods 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 10
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 9
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 9
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 9
- 230000000694 effects Effects 0.000 claims 9
- 125000004193 piperazinyl group Chemical group 0.000 claims 9
- 230000002159 abnormal effect Effects 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- 230000002378 acidificating effect Effects 0.000 claims 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 150000002828 nitro derivatives Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 3
- 241000534944 Thia Species 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 230000004968 inflammatory condition Effects 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 206010061598 Immunodeficiency Diseases 0.000 claims 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 208000019069 chronic childhood arthritis Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000007813 immunodeficiency Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 230000000306 recurrent effect Effects 0.000 claims 2
- 201000003068 rheumatic fever Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 201000003874 Common Variable Immunodeficiency Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000007452 Plasmacytoma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 235000009754 Vitis X bourquina Nutrition 0.000 claims 1
- 235000012333 Vitis X labruscana Nutrition 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000014787 Vitis vinifera Nutrition 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 206010002022 amyloidosis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000005784 autoimmunity Effects 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000017760 chronic graft versus host disease Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- WRTMOQVDBQDRNW-UHFFFAOYSA-N methyl 10-chloro-1-methyl-8-piperazin-1-yl-6h-benzo[b][1,5]benzoxathiepine-3-carboxylate;hydrochloride Chemical compound Cl.C1=C2CSC3=CC(C(=O)OC)=CC(C)=C3OC2=C(Cl)C=C1N1CCNCC1 WRTMOQVDBQDRNW-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 13
- 0 CCc(c(*)c(*)c(*)c1*)c1Oc1c(*)c(*)c(*)c(*)c1C Chemical compound CCc(c(*)c(*)c(*)c1*)c1Oc1c(*)c(*)c(*)c(*)c1C 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1226MU2004 | 2004-11-10 | ||
| US63721704P | 2004-12-17 | 2004-12-17 | |
| PCT/IB2005/053654 WO2006051477A2 (en) | 2004-11-10 | 2005-11-08 | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008519824A JP2008519824A (ja) | 2008-06-12 |
| JP2008519824A5 true JP2008519824A5 (https=) | 2009-08-13 |
Family
ID=38654748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007540782A Ceased JP2008519824A (ja) | 2004-11-10 | 2005-11-08 | 腫瘍壊死因子アルファの阻害剤としての縮合三環系化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US7834052B2 (https=) |
| EP (1) | EP1812419A2 (https=) |
| JP (1) | JP2008519824A (https=) |
| KR (1) | KR20070106981A (https=) |
| CN (1) | CN101076525B (https=) |
| AR (1) | AR056861A1 (https=) |
| AU (1) | AU2005303410B2 (https=) |
| CA (1) | CA2587671A1 (https=) |
| IL (2) | IL183038A0 (https=) |
| MX (1) | MX2007005470A (https=) |
| NZ (1) | NZ554937A (https=) |
| RU (1) | RU2406724C2 (https=) |
| TW (1) | TW200615273A (https=) |
| WO (1) | WO2006051477A2 (https=) |
| ZA (1) | ZA200703712B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010111673A1 (en) | 2009-03-27 | 2010-09-30 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic hcv inhibitors |
| CA2772085A1 (en) | 2009-08-27 | 2011-03-03 | The U.S.A., As Represented By The Secretary, Dept. Of Health And Human S Ervices | Compounds that treat malaria and prevent malaria transmission |
| WO2011075375A1 (en) * | 2009-12-14 | 2011-06-23 | Schering Corporation | Fused tricyclic compounds for the treatment of inflammatory disorders |
| HRP20140005T1 (hr) * | 2009-12-18 | 2014-01-31 | Basilea Pharmaceutica Ag | Tricikliäśki antibiotici |
| WO2012040389A2 (en) | 2010-09-22 | 2012-03-29 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic hcv inhibitors |
| WO2012050918A2 (en) * | 2010-09-29 | 2012-04-19 | Presidio Pharmaceutical, Inc. | Tricyclic fused ring inhibitors of hepatitis c |
| GB201507903D0 (en) * | 2015-05-08 | 2015-06-24 | Oncopeptides Ab | Process for preparation of nitrogen mustard derivatives |
| CN106995382A (zh) * | 2016-01-25 | 2017-08-01 | 济南和润化工科技有限公司 | 一种催化氢化法生产3-甲基-4-氨基苯甲酸的方法 |
| EA201892153A1 (ru) * | 2016-04-01 | 2019-04-30 | Юсб Байофарма Спрл | Конденсированные пентациклические производные имидазола в качестве модуляторов активности tnf |
| US10766906B2 (en) * | 2016-04-01 | 2020-09-08 | UCB Biopharma SRL | Fused hexacyclic imidazole derivatives as modulators of TNF activity |
| JP6968090B2 (ja) * | 2016-04-01 | 2021-11-17 | ユーシービー バイオファルマ エスアールエル | Ｔｎｆ活性のモジュレーターとしての縮合五環式イミダゾール誘導体 |
| EP3436458B1 (en) * | 2016-04-01 | 2021-06-02 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| CN106831460A (zh) * | 2017-02-24 | 2017-06-13 | 青铜峡市嘉华化工有限公司 | 3‑甲基‑4‑氨基苯甲酸的制备方法 |
| USD817148S1 (en) * | 2017-04-05 | 2018-05-08 | Dormakaba Canada Inc. | Locking system housing |
| CN107501106A (zh) * | 2017-08-14 | 2017-12-22 | 中涛新材料有限公司 | 一种催化加氢制备3‑甲基‑4‑氨基苯甲酸的方法 |
| WO2020179859A1 (ja) | 2019-03-06 | 2020-09-10 | 第一三共株式会社 | ピロロピラゾール誘導体 |
| CN115010621B (zh) * | 2022-07-21 | 2023-11-03 | 山东百启生物医药有限公司 | 一种4-溴-3-甲基苯甲腈的合成方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48807A0 (en) * | 1975-02-18 | 1976-03-31 | Syntex Inc | Novel 6,11-dihydrodibenzo-thiepin-11-ones,their preparation and compositions containing them |
| US4130654A (en) * | 1978-01-30 | 1978-12-19 | Syntex (U.S.A.) Inc. | Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof |
| IL57077A0 (en) * | 1978-04-21 | 1979-07-25 | Syntex Inc | 6,11-dihydrodibenzo-thiepin-11-one s-oxides their preparation and pharmaceutical compositions containing them |
| GB2094790B (en) * | 1981-03-13 | 1985-10-09 | Spofa Vereinigte Pharma Werke | Tricycle compounds |
| JPH0240662A (ja) | 1988-08-01 | 1990-02-09 | Ricoh Co Ltd | 電子写真用感光体 |
| US5036067A (en) | 1990-03-14 | 1991-07-30 | Merck & Co., Inc. | Dibenzoheterocyclic hydroxamic acids and hydroxy ureas as inhibitors of 5-lipoxygenase |
| JPH08119920A (ja) | 1994-10-18 | 1996-05-14 | Kyowa Hakko Kogyo Co Ltd | 三環式アニリド誘導体 |
| US5698551A (en) | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| JPH0940662A (ja) | 1995-05-24 | 1997-02-10 | Kyowa Hakko Kogyo Co Ltd | 三環式化合物 |
| IT1283637B1 (it) * | 1996-05-14 | 1998-04-23 | Italfarmaco Spa | Composti ad attivita' antinfiammatoria ed immunosoppressiva |
| JPH11130772A (ja) | 1997-10-28 | 1999-05-18 | Kyowa Hakko Kogyo Co Ltd | 含窒素複素環化合物 |
| AR014195A1 (es) | 1997-12-29 | 2001-02-07 | Ortho Mcneil Pharm Inc | Compuestos de trifenilpropanamida utiles para el tratamiento de procesos inflamatorios, composiciones anti-inflamatorias que los comprenden, ymetodos para prepararlos |
| TW200614995A (en) * | 2004-11-10 | 2006-05-16 | Nicholas Piramal India Ltd | Tricyclic guanidine derivatives as sodium-proton exchange inhibitors |
-
2005
- 2005-10-31 TW TW094138179A patent/TW200615273A/zh unknown
- 2005-11-08 CN CN2005800426605A patent/CN101076525B/zh not_active Expired - Fee Related
- 2005-11-08 RU RU2007121682/04A patent/RU2406724C2/ru not_active IP Right Cessation
- 2005-11-08 KR KR1020077013140A patent/KR20070106981A/ko not_active Ceased
- 2005-11-08 US US11/667,580 patent/US7834052B2/en not_active Expired - Fee Related
- 2005-11-08 EP EP05801266A patent/EP1812419A2/en not_active Withdrawn
- 2005-11-08 CA CA002587671A patent/CA2587671A1/en not_active Abandoned
- 2005-11-08 WO PCT/IB2005/053654 patent/WO2006051477A2/en not_active Ceased
- 2005-11-08 NZ NZ554937A patent/NZ554937A/en not_active IP Right Cessation
- 2005-11-08 JP JP2007540782A patent/JP2008519824A/ja not_active Ceased
- 2005-11-08 MX MX2007005470A patent/MX2007005470A/es active IP Right Grant
- 2005-11-08 AU AU2005303410A patent/AU2005303410B2/en not_active Ceased
- 2005-11-10 AR ARP050104716A patent/AR056861A1/es not_active Application Discontinuation
-
2007
- 2007-05-07 IL IL183038A patent/IL183038A0/en not_active IP Right Cessation
- 2007-05-07 IL IL210036A patent/IL210036A0/en unknown
- 2007-05-08 ZA ZA200703712A patent/ZA200703712B/xx unknown
-
2010
- 2010-08-11 US US12/854,761 patent/US8163730B2/en not_active Expired - Fee Related
- 2010-08-11 US US12/854,745 patent/US7964631B2/en not_active Expired - Fee Related
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