JP2003518060A5 - - Google Patents
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- JP2003518060A5 JP2003518060A5 JP2001546641A JP2001546641A JP2003518060A5 JP 2003518060 A5 JP2003518060 A5 JP 2003518060A5 JP 2001546641 A JP2001546641 A JP 2001546641A JP 2001546641 A JP2001546641 A JP 2001546641A JP 2003518060 A5 JP2003518060 A5 JP 2003518060A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- carbon atoms
- acid derivative
- acyl
- hydroxamic acid
- 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.)
- Pending
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- -1 imidazolylmethyl Chemical group 0.000 claims 51
- 239000002253 acid Substances 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- 125000004432 carbon atom Chemical group C* 0.000 claims 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 241000124008 Mammalia Species 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002252 acyl group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 8
- 125000004442 acylamino group Chemical group 0.000 claims 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 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 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims 2
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- ABCGRFHYOYXEJV-UHFFFAOYSA-N 4-methylisoindole-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)NC2=O ABCGRFHYOYXEJV-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 241000102542 Kara Species 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- KPGBXYROPKMUOQ-UHFFFAOYSA-N [[3-(1,3-dioxobenzo[e]isoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoyl]amino] acetate Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)NOC(C)=O)N2C(C3=C4C=CC=CC4=CC=C3C2=O)=O)=C1 KPGBXYROPKMUOQ-UHFFFAOYSA-N 0.000 claims 1
- GZFZOEHTHBPADL-UHFFFAOYSA-N [[3-(1,3-dioxoisoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoyl]amino] pentanoate Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(CC(=O)NOC(=O)CCCC)C1=CC=C(OC)C(OCC)=C1 GZFZOEHTHBPADL-UHFFFAOYSA-N 0.000 claims 1
- RKUKMEJKLRORIR-UHFFFAOYSA-N [[3-(1,3-dioxoisoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoyl]amino] propanoate Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)NOC(=O)CC)N2C(C3=CC=CC=C3C2=O)=O)=C1 RKUKMEJKLRORIR-UHFFFAOYSA-N 0.000 claims 1
- VJTXUIHFOFREFB-UHFFFAOYSA-N [[3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(5-methyl-1,3-dioxoisoindol-2-yl)propanoyl]amino] acetate Chemical compound COC1=CC=C(C(CC(=O)NOC(C)=O)N2C(C3=CC(C)=CC=C3C2=O)=O)C=C1OC1CCCC1 VJTXUIHFOFREFB-UHFFFAOYSA-N 0.000 claims 1
- UIGKRPMDNHMRCE-UHFFFAOYSA-N [[3-(3-ethoxy-4-methoxyphenyl)-3-(4-methyl-1,3-dioxoisoindol-2-yl)propanoyl]amino] acetate Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)NOC(C)=O)N2C(C3=C(C)C=CC=C3C2=O)=O)=C1 UIGKRPMDNHMRCE-UHFFFAOYSA-N 0.000 claims 1
- TZYJLDLGDKPCJN-UHFFFAOYSA-N [[3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoyl]-acetylamino] acetate Chemical compound COC1=CC=C(C(CC(=O)N(OC(C)=O)C(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)C=C1OC1CCCC1 TZYJLDLGDKPCJN-UHFFFAOYSA-N 0.000 claims 1
- MBEKEDVTWGAHSR-UHFFFAOYSA-N [[3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoyl]amino] acetate Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)NOC(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 MBEKEDVTWGAHSR-UHFFFAOYSA-N 0.000 claims 1
- MTUSUIOBWDPHJZ-UHFFFAOYSA-N [[3-(5-acetamido-1,3-dioxoisoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoyl]amino] acetate Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)NOC(C)=O)N2C(C3=CC(NC(C)=O)=CC=C3C2=O)=O)=C1 MTUSUIOBWDPHJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 208000002399 aphthous stomatitis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 208000020670 canker sore Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/468,529 US6699899B1 (en) | 1999-12-21 | 1999-12-21 | Substituted acylhydroxamic acids and method of reducing TNFα levels |
| US09/468,529 | 1999-12-21 | ||
| PCT/US2000/034455 WO2001045702A1 (en) | 1999-12-21 | 2000-12-19 | SUBSTITUTED ACYLHYDROXAMIC ACIDS AND METHOD OF REDUCING TNFα LEVELS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003518060A JP2003518060A (ja) | 2003-06-03 |
| JP2003518060A5 true JP2003518060A5 (enExample) | 2005-06-09 |
Family
ID=23860180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001546641A Pending JP2003518060A (ja) | 1999-12-21 | 2000-12-19 | 置換アシルヒドロキサム酸およびＴＮＦαレベルの減少方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US6699899B1 (enExample) |
| EP (1) | EP1246620A4 (enExample) |
| JP (1) | JP2003518060A (enExample) |
| KR (2) | KR20070086919A (enExample) |
| CN (1) | CN1413109A (enExample) |
| AU (1) | AU782634B2 (enExample) |
| CA (1) | CA2394604A1 (enExample) |
| FI (1) | FI20021193A7 (enExample) |
| HK (1) | HK1050625A1 (enExample) |
| MX (1) | MXPA02005840A (enExample) |
| NO (2) | NO323515B1 (enExample) |
| NZ (1) | NZ519638A (enExample) |
| TW (2) | TWI282788B (enExample) |
| WO (1) | WO2001045702A1 (enExample) |
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| US6699899B1 (en) * | 1999-12-21 | 2004-03-02 | Celgene Corporation | Substituted acylhydroxamic acids and method of reducing TNFα levels |
| US8030343B2 (en) * | 2000-06-08 | 2011-10-04 | Celgene Corporation | Pharmaceutically active isoindoline derivatives |
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| US20100129363A1 (en) * | 2002-05-17 | 2010-05-27 | Zeldis Jerome B | Methods and compositions using pde4 inhibitors for the treatment and management of cancers |
| CA2501936A1 (en) * | 2002-10-15 | 2004-04-29 | Celgene Corporation | Selective cytokine inhibitory drugs for treating myelodysplastic syndrome |
| US20040087558A1 (en) * | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment, modification and management of pain |
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| CA2505131A1 (en) | 2002-11-06 | 2004-05-27 | Celgene Corporation | Methods and compositions using selective cytokine inhibitory drugs for treatment and management of cancers and other diseases |
| KR20050072790A (ko) * | 2002-11-06 | 2005-07-12 | 셀진 코포레이션 | 골수증식 질환의 치료 및 관리를 위한 선택적 시토킨 억제약물의 사용 방법 및 이를 포함하는 조성물 |
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| KR20050090435A (ko) | 2002-12-30 | 2005-09-13 | 셀진 코포레이션 | 플루오로알콕시-치환된 1,3-디히드로-이소인돌릴 화합물 및그의 제약학적 용도 |
| US20040175382A1 (en) * | 2003-03-06 | 2004-09-09 | Schafer Peter H. | Methods of using and compositions comprising selective cytokine inhibitory drugs for the treatment and management of disorders of the central nervous system |
| CN100427465C (zh) * | 2003-03-12 | 2008-10-22 | 细胞基因公司 | N-烷基-异羟肟酸-异吲哚基化合物及其药物用途 |
| BRPI0408223A (pt) * | 2003-03-12 | 2006-03-01 | Celgene Corp | composto, isÈmeros, composição farmacêutica, e, métodos de inibir pde4 e mmp, de modular a produção de tnf-alfa em um mamìfero e de tratar, previnir ou controlar uma doença ou condição |
| ES2362484T3 (es) * | 2003-03-12 | 2011-07-06 | Celgene Corporation | Compuestos de ácido n-alquil-hidroxámico-isoindolilo y sus usos farmacéuticos. |
| US20050142104A1 (en) * | 2003-11-06 | 2005-06-30 | Zeldis Jerome B. | Methods of using and compositions comprising PDE4 modulators for the treatment and management of asbestos-related diseases and disorders |
| WO2005097747A1 (en) * | 2004-04-05 | 2005-10-20 | Aton Pharma, Inc. | Histone deacetylase inhibitor prodrugs |
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| US10682336B2 (en) | 2015-10-21 | 2020-06-16 | Amgen Inc. | PDE4 modulators for treating and preventing immune reconstitution inflammatory syndrome (IRIS) |
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| CA2295295A1 (en) * | 1997-07-31 | 1999-02-11 | Celgene Corporation | Substituted alkanohydroxamic acids and method of reducing tnf.alpha. levels |
| CA2308361A1 (en) * | 1997-11-12 | 1999-05-20 | Andrew Douglas Baxter | Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity |
| US6020358A (en) | 1998-10-30 | 2000-02-01 | Celgene Corporation | Substituted phenethylsulfones and method of reducing TNFα levels |
| US6699899B1 (en) * | 1999-12-21 | 2004-03-02 | Celgene Corporation | Substituted acylhydroxamic acids and method of reducing TNFα levels |
| BRPI0408223A (pt) * | 2003-03-12 | 2006-03-01 | Celgene Corp | composto, isÈmeros, composição farmacêutica, e, métodos de inibir pde4 e mmp, de modular a produção de tnf-alfa em um mamìfero e de tratar, previnir ou controlar uma doença ou condição |
-
1999
- 1999-12-21 US US09/468,529 patent/US6699899B1/en not_active Expired - Fee Related
-
2000
- 2000-12-12 TW TW089125922A patent/TWI282788B/zh active
- 2000-12-12 TW TW095124062A patent/TWI295925B/zh not_active IP Right Cessation
- 2000-12-19 WO PCT/US2000/034455 patent/WO2001045702A1/en not_active Ceased
- 2000-12-19 HK HK03101278.8A patent/HK1050625A1/zh unknown
- 2000-12-19 NZ NZ519638A patent/NZ519638A/en unknown
- 2000-12-19 JP JP2001546641A patent/JP2003518060A/ja active Pending
- 2000-12-19 EP EP00988151A patent/EP1246620A4/en not_active Withdrawn
- 2000-12-19 CN CN00817538A patent/CN1413109A/zh active Pending
- 2000-12-19 CA CA002394604A patent/CA2394604A1/en not_active Abandoned
- 2000-12-19 KR KR1020077015292A patent/KR20070086919A/ko not_active Ceased
- 2000-12-19 MX MXPA02005840A patent/MXPA02005840A/es active IP Right Grant
- 2000-12-19 KR KR1020027007915A patent/KR100831339B1/ko not_active Expired - Fee Related
- 2000-12-19 AU AU24389/01A patent/AU782634B2/en not_active Ceased
-
2002
- 2002-06-18 NO NO20022936A patent/NO323515B1/no not_active IP Right Cessation
- 2002-06-19 FI FI20021193A patent/FI20021193A7/fi not_active Application Discontinuation
-
2004
- 2004-02-25 US US10/786,822 patent/US7345062B2/en not_active Expired - Fee Related
-
2007
- 2007-03-21 NO NO20071498A patent/NO20071498L/no not_active Application Discontinuation
-
2008
- 2008-01-16 US US12/009,182 patent/US20080280967A1/en not_active Abandoned
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