EA030539B1 - Производные 1-амино-2-циклобутилэтилбороновой кислоты - Google Patents

Info

Publication number

EA030539B1

EA030539B1 EA201170508A EA201170508A EA030539B1 EA 030539 B1 EA030539 B1 EA 030539B1 EA 201170508 A EA201170508 A EA 201170508A EA 201170508 A EA201170508 A EA 201170508A EA 030539 B1 EA030539 B1 EA 030539B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

cyclobutyl

ethyl

boronic acid

phenyl

Prior art date

2008-09-29

Links

• Espacenet
• Global Dossier
• Discuss

• BCNMPHGGRXUKHU-UHFFFAOYSA-N (1-amino-2-cyclobutylethyl)boronic acid Chemical class OB(O)C(N)CC1CCC1 BCNMPHGGRXUKHU-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 115
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 12
• -1 {(2S) -2- [(2,5dichlorobenzoyl) amino] -3phenylpropanoyl} amino Chemical group 0.000 claims description 112
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 80
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 31
• 125000001931 aliphatic group Chemical group 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 22
• 201000011510 cancer Diseases 0.000 claims description 20
• 239000012634 fragment Substances 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 150000008064 anhydrides Chemical class 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 13
• 235000010355 mannitol Nutrition 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
• 229940124597 therapeutic agent Drugs 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 8
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
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• 229910052796 boron Inorganic materials 0.000 claims description 7
• 125000006162 fluoroaliphatic group Chemical group 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 239000000594 mannitol Substances 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• PAVZHTXVORCEHP-UHFFFAOYSA-N ethylboronic acid Chemical compound CCB(O)O PAVZHTXVORCEHP-UHFFFAOYSA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 3
• 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 claims description 3
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 3
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• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• LEPWUMPXISBPIB-UHFFFAOYSA-N 4-phenylbutanamide Chemical compound NC(=O)CCCC1=CC=CC=C1 LEPWUMPXISBPIB-UHFFFAOYSA-N 0.000 claims description 2
• IVPOYVAYCDRKIH-UIOOFZCWSA-N [(1r)-2-cyclobutyl-1-[[(2s)-3-[(4-methylbenzoyl)amino]-2-[(6-phenylpyridine-2-carbonyl)amino]propanoyl]amino]ethyl]boronic acid Chemical compound C1=CC(C)=CC=C1C(=O)NC[C@@H](C(=O)N[C@@H](CC1CCC1)B(O)O)NC(=O)C1=CC=CC(C=2C=CC=CC=2)=N1 IVPOYVAYCDRKIH-UIOOFZCWSA-N 0.000 claims description 2
• RNASGPQQKQIXHE-GKCIPKSASA-N [(1r)-2-cyclobutyl-1-[[(2s,3s)-3-hydroxy-2-[(6-phenylpyridine-2-carbonyl)amino]butanoyl]amino]ethyl]boronic acid Chemical compound N([C@@H]([C@@H](O)C)C(=O)N[C@@H](CC1CCC1)B(O)O)C(=O)C(N=1)=CC=CC=1C1=CC=CC=C1 RNASGPQQKQIXHE-GKCIPKSASA-N 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims description 2
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• ISUVIHKZBIDXQH-ZEQRLZLVSA-N [(1r)-2-cyclobutyl-1-[[(2s)-2-(naphthalen-2-ylsulfonylamino)-3-phenylpropanoyl]amino]ethyl]boronic acid Chemical compound C([C@@H](B(O)O)NC(=O)[C@H](CC=1C=CC=CC=1)NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)C1CCC1 ISUVIHKZBIDXQH-ZEQRLZLVSA-N 0.000 claims 1
• HIMZKLZYUSSSIR-ZEQRLZLVSA-N [(1r)-2-cyclobutyl-1-[[(2s)-2-[(2-phenoxypyridine-3-carbonyl)amino]-3-phenylpropanoyl]amino]ethyl]boronic acid Chemical compound C([C@@H](B(O)O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C(=NC=CC=1)OC=1C=CC=CC=1)C1CCC1 HIMZKLZYUSSSIR-ZEQRLZLVSA-N 0.000 claims 1
• MFJIGOGMDFJPAH-UIOOFZCWSA-N [(1r)-2-cyclobutyl-1-[[(2s)-2-[(3-phenoxybenzoyl)amino]-3-phenylpropanoyl]amino]ethyl]boronic acid Chemical compound C([C@@H](B(O)O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1CCC1 MFJIGOGMDFJPAH-UIOOFZCWSA-N 0.000 claims 1
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