JP2005501005A5 - - Google Patents
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- Publication number
- JP2005501005A5 JP2005501005A5 JP2003500112A JP2003500112A JP2005501005A5 JP 2005501005 A5 JP2005501005 A5 JP 2005501005A5 JP 2003500112 A JP2003500112 A JP 2003500112A JP 2003500112 A JP2003500112 A JP 2003500112A JP 2005501005 A5 JP2005501005 A5 JP 2005501005A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- propionylamino
- ylamino
- biphenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 biphenylyl Chemical group 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 8
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- MIFUSOBKODRKPC-OLWNVYNHSA-N [(1r)-3-methyl-1-[[(2s)-4-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]pentanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 MIFUSOBKODRKPC-OLWNVYNHSA-N 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- YYXCDWMJTBCHJW-AIUMHDJVSA-N pubchem11583 Chemical compound C1[C@@]2([H])C(C)(C)[C@]1([H])C[C@H]1OB([C@@H](N)CC(C)C)O[C@]12C YYXCDWMJTBCHJW-AIUMHDJVSA-N 0.000 claims 2
- RVMYSKJBWGAPPQ-DQEYMECFSA-N (2s)-2-[[(2s)-3-(3,4-dimethoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]-4-methylpentanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC1=CC=CC(C=2C=CC=CC=2)=C1 RVMYSKJBWGAPPQ-DQEYMECFSA-N 0.000 claims 1
- VOLLGGPORYHKST-UIOOFZCWSA-N (2s)-2-[[(2s)-3-(4-methoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]-4-methylpentanoic acid Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC1=CC=CC(C=2C=CC=CC=2)=C1 VOLLGGPORYHKST-UIOOFZCWSA-N 0.000 claims 1
- MQTFRDWVOXMYPD-NQAOIOOJSA-N (2s)-3-methyl-n-[3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl]-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanamide Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)NC(CC(C)C)B2OC(C)(C)C(C)(C)O2)=C1 MQTFRDWVOXMYPD-NQAOIOOJSA-N 0.000 claims 1
- QWWDLTHXPFKTAS-DQEYMECFSA-N (2s)-4-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]pentanoic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](CC(C)C)C(O)=O)=C1 QWWDLTHXPFKTAS-DQEYMECFSA-N 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- CCMMLNAYXJIYSX-NAYUSWPISA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(3,4-dimethoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 CCMMLNAYXJIYSX-NAYUSWPISA-N 0.000 claims 1
- SIVDXIDADYCFIS-VFXRXZKFSA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(3,4-dimethoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]propanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 SIVDXIDADYCFIS-VFXRXZKFSA-N 0.000 claims 1
- BIGIFWJGBNONPK-APGVRMINSA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(3,4-dimethoxyphenyl)-2-[[2-(3-phenoxyphenyl)acetyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 BIGIFWJGBNONPK-APGVRMINSA-N 0.000 claims 1
- NOCYZLFJDNEMRY-DTXPUJKBSA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(4-methoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 NOCYZLFJDNEMRY-DTXPUJKBSA-N 0.000 claims 1
- BCRCUSHGQVRUGQ-CHQNGUEUSA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(4-methoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 BCRCUSHGQVRUGQ-CHQNGUEUSA-N 0.000 claims 1
- JPHIPLCHJZGVRY-NUKCWJJBSA-N [(1r)-1-[[(2s)-2-[[(2s)-3-(4-methoxyphenyl)-2-(3-phenylanilino)propanoyl]amino]propanoyl]amino]-3-methylbutyl]boronic acid Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 JPHIPLCHJZGVRY-NUKCWJJBSA-N 0.000 claims 1
- CFKMEDWCTRYERJ-SKTSAMEXSA-N [(1r)-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]-2-phenylethyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=2C=CC=CC=2)B(O)O)=C1 CFKMEDWCTRYERJ-SKTSAMEXSA-N 0.000 claims 1
- XZXKVJSYPUKVEO-FKCXQASGSA-N [(1r)-3-methyl-1-[[(2r)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 XZXKVJSYPUKVEO-FKCXQASGSA-N 0.000 claims 1
- LCDJPEAMOSFROR-PTJQVGQKSA-N [(1r)-3-methyl-1-[[(2s)-2-[[(2s)-2-(3-phenylanilino)-3-(2,3,4-trimethoxyphenyl)propanoyl]amino]propanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 LCDJPEAMOSFROR-PTJQVGQKSA-N 0.000 claims 1
- PZFHDQKICAUUFL-VFXRXZKFSA-N [(1r)-3-methyl-1-[[(2s)-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]propanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 PZFHDQKICAUUFL-VFXRXZKFSA-N 0.000 claims 1
- URJILNGJEMDJRO-APTRMMRNSA-N [(1r)-3-methyl-1-[[(2s)-2-[[(2s)-2-(3-phenylpropanoylamino)-3-(2,3,4-trimethoxyphenyl)propanoyl]amino]propanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)CCC1=CC=CC=C1 URJILNGJEMDJRO-APTRMMRNSA-N 0.000 claims 1
- JTORVSLPMVHQGA-CZZAQMAHSA-N [(1r)-3-methyl-1-[[(2s)-2-[[(2s)-2-(3-propan-2-ylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]propanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 JTORVSLPMVHQGA-CZZAQMAHSA-N 0.000 claims 1
- XZXKVJSYPUKVEO-RDAHNBDFSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2r)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 XZXKVJSYPUKVEO-RDAHNBDFSA-N 0.000 claims 1
- HHKANKSMOJBZQU-BKHJTQGXSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(2,3,4-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC1=CC=CC(C=2C=CC=CC=2)=C1 HHKANKSMOJBZQU-BKHJTQGXSA-N 0.000 claims 1
- XZXKVJSYPUKVEO-NAYUSWPISA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 XZXKVJSYPUKVEO-NAYUSWPISA-N 0.000 claims 1
- WIVSRPZCCCWNPC-KVBYWJEESA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(4-phenylmethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)B(O)O)C(C)C)NC=1C=C(C=CC=1)C=1C=CC=CC=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 WIVSRPZCCCWNPC-KVBYWJEESA-N 0.000 claims 1
- QXEUNGISQGCLFR-WIRXVTQYSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-propan-2-ylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 QXEUNGISQGCLFR-WIRXVTQYSA-N 0.000 claims 1
- ZZICOHYGCXGTAI-NSGJQZOKSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-pyridin-2-ylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2N=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 ZZICOHYGCXGTAI-NSGJQZOKSA-N 0.000 claims 1
- NGYRVQBQNSJZRR-LVCXIWIQSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-[[2-(3-phenoxyphenyl)acetyl]amino]-3-(2,3,4-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 NGYRVQBQNSJZRR-LVCXIWIQSA-N 0.000 claims 1
- RLOQPEJQOUDYSP-APGVRMINSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-[[2-(3-phenoxyphenyl)acetyl]amino]-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC(=O)CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)B(O)O)=C1 RLOQPEJQOUDYSP-APGVRMINSA-N 0.000 claims 1
- HPBDHYQLLUCSOT-UZGNFBRWSA-N [(1r)-3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-3-(4-phenylmethoxyphenyl)-2-[[2-(3-phenylmethoxyphenyl)acetyl]amino]propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)B(O)O)C(C)C)NC(=O)CC=1C=C(OCC=2C=CC=CC=2)C=CC=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 HPBDHYQLLUCSOT-UZGNFBRWSA-N 0.000 claims 1
- XZXKVJSYPUKVEO-VKLABOROSA-N [3-methyl-1-[[(2s)-3-methyl-2-[[(2s)-2-(3-phenylanilino)-3-(3,4,5-trimethoxyphenyl)propanoyl]amino]butanoyl]amino]butyl]boronic acid Chemical compound COC1=C(OC)C(OC)=CC(C[C@H](NC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)N[C@@H](C(C)C)C(=O)NC(CC(C)C)B(O)O)=C1 XZXKVJSYPUKVEO-VKLABOROSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- RGTLYZSQOQHZAT-UHFFFAOYSA-N pentan-2-ylboronic acid Chemical compound CCCC(C)B(O)O RGTLYZSQOQHZAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 108090000708 Proteasome Endopeptidase Complex Proteins 0.000 description 6
- 102000004245 Proteasome Endopeptidase Complex Human genes 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 108010022579 ATP dependent 26S protease Proteins 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 102000044159 Ubiquitin Human genes 0.000 description 1
- 108090000848 Ubiquitin Proteins 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000037012 chymotrypsin-like activity Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0113096A GB0113096D0 (en) | 2001-05-30 | 2001-05-30 | Organic compounds |
| GB0129394A GB0129394D0 (en) | 2001-12-07 | 2001-12-07 | Organic compounds |
| PCT/EP2002/005937 WO2002096933A1 (en) | 2001-05-30 | 2002-05-29 | 2-{[n-(2-amino-3-(heteroaryl or aryl)propionyl)-aminoacyl]-amino}-alkylboronic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005501005A JP2005501005A (ja) | 2005-01-13 |
| JP2005501005A5 true JP2005501005A5 (https=) | 2009-11-05 |
| JP4416501B2 JP4416501B2 (ja) | 2010-02-17 |
Family
ID=26246132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003500112A Expired - Fee Related JP4416501B2 (ja) | 2001-05-30 | 2002-05-29 | ２−｛［ｎ−（２−アミノ−３−（ヘテロアリールまたはアリール）プロピオニル）−アミノアシル］−アミノ｝−アルキルボロン酸誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6933290B2 (https=) |
| EP (1) | EP1399468B1 (https=) |
| JP (1) | JP4416501B2 (https=) |
| CN (1) | CN100415770C (https=) |
| AT (1) | ATE317850T1 (https=) |
| BR (1) | BR0210112A (https=) |
| CA (1) | CA2446282A1 (https=) |
| DE (1) | DE60209227T2 (https=) |
| ES (1) | ES2258149T3 (https=) |
| PT (1) | PT1399468E (https=) |
| WO (1) | WO2002096933A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60209227T2 (de) * | 2001-05-30 | 2006-08-17 | Novartis Ag | 2-((n-(2-amino-3-(heteroaryl- oder -aryl)propionyl)aminoacyl)amino)-alkylboronsäurederivate |
| JP4412586B2 (ja) | 2002-01-08 | 2010-02-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | エポネマイシンおよびエポキソマイシン類似物およびそれらの用途 |
| CA2505361A1 (en) * | 2002-11-11 | 2004-05-27 | Bayer Healthcare Ag | Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist |
| US7223745B2 (en) | 2003-08-14 | 2007-05-29 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US7576206B2 (en) | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US7468383B2 (en) | 2005-02-11 | 2008-12-23 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| CA2618513A1 (en) | 2005-08-11 | 2007-02-22 | Ariad Pharmaceuticals, Inc. | Unsaturated heterocyclic derivatives |
| CA2629714A1 (en) | 2005-11-14 | 2007-05-24 | Ariad Gene Therapeutics, Inc. | Administration of an mtor inhibitor to treat patients with cancer |
| SI2495016T1 (sl) | 2005-12-23 | 2020-04-30 | Ariad Pharmaceuticals, Inc. | Biciklične heteroarilne spojine |
| AU2007357338B2 (en) | 2007-08-06 | 2014-03-20 | Takeda Pharmaceutical Company Limited | Proteasome inhibitors |
| PT2300013T (pt) | 2008-05-21 | 2017-10-31 | Ariad Pharma Inc | Derivados de fósforo como inibidores de cinases |
| CA2727862C (en) | 2008-06-17 | 2016-04-19 | Millennium Pharmaceuticals, Inc. | Boronate ester compounds and pharmaceutical compositions thereof |
| AR075090A1 (es) | 2008-09-29 | 2011-03-09 | Millennium Pharm Inc | Derivados de acido 1-amino-2-ciclobutiletilboronico inhibidores de proteosoma,utiles como agentes anticancerigenos, y composiciones farmaceuticas que los comprenden. |
| EP2365809B8 (en) | 2008-11-12 | 2018-10-10 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| WO2010096574A1 (en) | 2009-02-20 | 2010-08-26 | Lisanti Michael P | A method of diagnosis or prognosis of a neoplasm comprising determining the level of expression of a protein in stromal cells adjacent to the neoplasm |
| AU2010341530B2 (en) | 2009-12-22 | 2016-03-10 | Cephalon, Inc. | Proteasome inhibitors and processes for their preparation, purification and use |
| CA2791651C (en) * | 2010-03-01 | 2019-08-20 | Onyx Therapeutics, Inc. | Compounds for immunoproteasome inhibition |
| WO2011133479A2 (en) | 2010-04-19 | 2011-10-27 | Niiki Pharma Inc. | Combination therapy with a proteasome inhibitor and a gallium complex |
| GB2523211B (en) | 2012-01-27 | 2020-03-18 | Univ Jefferson | MCT protein inhibitor-related prognostic and therapeutic methods |
| CN103421032B (zh) * | 2012-05-17 | 2016-01-20 | 上海创诺制药有限公司 | 一种硼替佐米中间体及其制备方法和应用 |
| WO2014172627A1 (en) | 2013-04-19 | 2014-10-23 | Thomas Jefferson University | Caveolin-1 related methods for treating glioblastoma with temozolomide |
| TN2016000492A1 (en) | 2014-05-20 | 2018-04-04 | Millennium Pharm Inc | Boron-containing proteasome inhibitors for use after primary cancer therapy. |
| CN110526912B (zh) | 2014-06-19 | 2023-02-14 | 武田药品工业株式会社 | 用于激酶抑制的杂芳基化合物 |
| MA41505A (fr) | 2015-02-11 | 2017-12-19 | Millennium Pharm Inc | Nouvelle forme cristalline d'un inhibiteur de protéasome |
| HUE064412T2 (hu) | 2016-06-21 | 2024-03-28 | Orion Ophthalmology LLC | Heterociklusos prolinamid-származékok |
| JP7164521B2 (ja) | 2016-06-21 | 2022-11-01 | オリオン・オフサルモロジー・エルエルシー | 炭素環式プロリンアミド誘導体 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499082A (en) | 1983-12-05 | 1985-02-12 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid peptides |
| EP0315574A3 (de) | 1987-11-05 | 1990-08-22 | Hoechst Aktiengesellschaft | Renin-Inhibitoren |
| US5106948A (en) * | 1988-05-27 | 1992-04-21 | Mao Foundation For Medical Education And Research | Cytotoxic boronic acid peptide analogs |
| GB9017694D0 (en) | 1990-08-13 | 1990-09-26 | Sandoz Ltd | Improvements in or relating to organic chemistry |
| US5384410A (en) | 1993-03-24 | 1995-01-24 | The Du Pont Merck Pharmaceutical Company | Removal of boronic acid protecting groups by transesterification |
| US5658885A (en) | 1993-04-27 | 1997-08-19 | The Dupont Merck Pharmaceutical Company | Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes |
| IL109319A0 (en) | 1993-04-27 | 1994-07-31 | Du Pont Merck Pharma | Amidino and guanidino substituted boronic acid compounds |
| FR2721611B1 (fr) * | 1994-06-22 | 1996-09-27 | Adir | Nouveaux dérivés peptidiques de l'acide boronique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent . |
| US6083903A (en) * | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
| US5614649A (en) | 1994-11-14 | 1997-03-25 | Cephalon, Inc. | Multicatalytic protease inhibitors |
| US5550262A (en) | 1994-11-14 | 1996-08-27 | Cephalon, Inc. | Multicatalytic protease inhibitors |
| CN1282242A (zh) | 1997-12-16 | 2001-01-31 | 赛福伦公司 | 多相催化蛋白酶抑制剂用作抗肿瘤剂 |
| DE60209227T2 (de) * | 2001-05-30 | 2006-08-17 | Novartis Ag | 2-((n-(2-amino-3-(heteroaryl- oder -aryl)propionyl)aminoacyl)amino)-alkylboronsäurederivate |
-
2002
- 2002-05-29 DE DE60209227T patent/DE60209227T2/de not_active Expired - Fee Related
- 2002-05-29 AT AT02743128T patent/ATE317850T1/de not_active IP Right Cessation
- 2002-05-29 CN CNB028108132A patent/CN100415770C/zh not_active Expired - Fee Related
- 2002-05-29 BR BR0210112-2A patent/BR0210112A/pt not_active IP Right Cessation
- 2002-05-29 JP JP2003500112A patent/JP4416501B2/ja not_active Expired - Fee Related
- 2002-05-29 PT PT02743128T patent/PT1399468E/pt unknown
- 2002-05-29 ES ES02743128T patent/ES2258149T3/es not_active Expired - Lifetime
- 2002-05-29 EP EP02743128A patent/EP1399468B1/en not_active Expired - Lifetime
- 2002-05-29 CA CA002446282A patent/CA2446282A1/en not_active Abandoned
- 2002-05-29 WO PCT/EP2002/005937 patent/WO2002096933A1/en not_active Ceased
- 2002-05-29 US US10/478,794 patent/US6933290B2/en not_active Expired - Fee Related
-
2005
- 2005-06-30 US US11/172,146 patent/US20050239716A1/en not_active Abandoned
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