JP2007536200A5

JP2007536200A5 -

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Publication number: JP2007536200A5
Authority: JP; Japan
Prior art keywords: acid; amphomycin; compound; substituted; amino acid
Prior art date: 2004-06-28
Legal status : Pending

Application number

JP2006520201A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007536200A (ja

Filing date

2004-06-28

Publication date

2010-10-28

2004-06-28 Application filed filed Critical

2004-06-28 Priority claimed from PCT/US2004/021039 external-priority patent/WO2005000878A2/en

2007-12-13 Publication of JP2007536200A publication Critical patent/JP2007536200A/ja

2010-10-28 Publication of JP2007536200A5 publication Critical patent/JP2007536200A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 565
238000000034 method Methods 0.000 claims description 313
-1 p-aminophenylacetyl Chemical group 0.000 claims description 208
150000001413 amino acids Chemical class 0.000 claims description 199
239000000203 mixture Substances 0.000 claims description 174
125000001424 substituent group Chemical group 0.000 claims description 84
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 73
208000015181 infectious disease Diseases 0.000 claims description 64
125000000217 alkyl group Chemical group 0.000 claims description 58
125000003710 aryl alkyl group Chemical group 0.000 claims description 58
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 57
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 55
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 42
125000000172 C5-C10 aryl group Chemical group 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 36
239000004471 Glycine Substances 0.000 claims description 34
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
238000002360 preparation method Methods 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 31
238000011282 treatment Methods 0.000 claims description 31
125000004404 heteroalkyl group Chemical group 0.000 claims description 30
150000005347 biaryls Chemical group 0.000 claims description 28
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 28
239000004472 Lysine Substances 0.000 claims description 27
125000005418 aryl aryl group Chemical group 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 27
125000001931 aliphatic group Chemical group 0.000 claims description 26
230000000813 microbial effect Effects 0.000 claims description 26
241000894006 Bacteria Species 0.000 claims description 25
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 25
229940000635 beta-alanine Drugs 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 23
125000006239 protecting group Chemical group 0.000 claims description 23
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
150000003335 secondary amines Chemical class 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
229960003692 gamma aminobutyric acid Drugs 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
150000003141 primary amines Chemical class 0.000 claims description 20
125000004953 trihalomethyl group Chemical group 0.000 claims description 18
229960004050 aminobenzoic acid Drugs 0.000 claims description 17
JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 claims description 16
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 16
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125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
108010077895 Sarcosine Proteins 0.000 claims description 14
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 14
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 12
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XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 8
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 8
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PCNFLKVWBDNNOW-UHFFFAOYSA-N 4-hydrazinylbenzoic acid Chemical compound NNC1=CC=C(C(O)=O)C=C1 PCNFLKVWBDNNOW-UHFFFAOYSA-N 0.000 claims description 6
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JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 6
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KFGVDCBVGNMCJC-UHFFFAOYSA-N 2-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC=C1C(O)=O KFGVDCBVGNMCJC-UHFFFAOYSA-N 0.000 claims description 5
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241000191963 Staphylococcus epidermidis Species 0.000 claims description 5
206010014665 endocarditis Diseases 0.000 claims description 5
VBYDSMBICNUTKN-UHFFFAOYSA-N 3-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC(C(O)=O)=C1 VBYDSMBICNUTKN-UHFFFAOYSA-N 0.000 claims description 4
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BKKWZCSSYWYNDS-JEDNCBNOSA-N 2-aminoacetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCC(O)=O.NCCCC[C@H](N)C(O)=O BKKWZCSSYWYNDS-JEDNCBNOSA-N 0.000 claims description 3
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208000024794 sputum Diseases 0.000 claims description 3
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JP2006520201A 2003-07-17 2004-06-28 リポペプチド抗生物質誘導体の組成物およびその使用方法 Pending JP2007536200A (ja)