JP4416501B2 - 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 - Google Patents
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 Download PDFInfo
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- JP4416501B2 JP4416501B2 JP2003500112A JP2003500112A JP4416501B2 JP 4416501 B2 JP4416501 B2 JP 4416501B2 JP 2003500112 A JP2003500112 A JP 2003500112A JP 2003500112 A JP2003500112 A JP 2003500112A JP 4416501 B2 JP4416501 B2 JP 4416501B2
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- Japan
- Prior art keywords
- methyl
- phenyl
- propionylamino
- biphenyl
- ylamino
- 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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- 125000003118 aryl group Chemical group 0.000 title abstract description 18
- 239000002253 acid Substances 0.000 title abstract description 15
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 title abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 246
- -1 biphenylyl Chemical group 0.000 claims description 169
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 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 description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 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 description 6
- 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 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 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
- 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
- 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
- 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
- 125000002887 hydroxy group Chemical group [H]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
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 75
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 64
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- 206010028980 Neoplasm Diseases 0.000 description 40
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 JP2005501005A5 (https=) | 2009-11-05 |
| JP4416501B2 true 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 |
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| 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 |
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| 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
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2005
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Also Published As
| Publication number | Publication date |
|---|---|
| US20050239716A1 (en) | 2005-10-27 |
| DE60209227T2 (de) | 2006-08-17 |
| US20040167337A1 (en) | 2004-08-26 |
| EP1399468B1 (en) | 2006-02-15 |
| CA2446282A1 (en) | 2002-12-05 |
| CN1512999A (zh) | 2004-07-14 |
| EP1399468A1 (en) | 2004-03-24 |
| ATE317850T1 (de) | 2006-03-15 |
| US6933290B2 (en) | 2005-08-23 |
| PT1399468E (pt) | 2006-05-31 |
| BR0210112A (pt) | 2004-06-08 |
| ES2258149T3 (es) | 2006-08-16 |
| WO2002096933A1 (en) | 2002-12-05 |
| JP2005501005A (ja) | 2005-01-13 |
| DE60209227D1 (de) | 2006-04-20 |
| CN100415770C (zh) | 2008-09-03 |
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