ZA200600008B - Compositions of lipopeptide antibiotic derivatives and methods of use thereof - Google Patents

Info

Publication number

ZA200600008B

ZA200600008B ZA200600008A ZA200600008A ZA200600008B ZA 200600008 B ZA200600008 B ZA 200600008B ZA 200600008 A ZA200600008 A ZA 200600008A ZA 200600008 A ZA200600008 A ZA 200600008A ZA 200600008 B ZA200600008 B ZA 200600008B

Authority

ZA

South Africa

Prior art keywords

compound

acid

amphomycin

substituted

amino acid

Prior art date

2003-07-17

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 454
• 108010028921 Lipopeptides Proteins 0.000 title description 192
• 239000000203 mixture Substances 0.000 title description 165
• 230000003115 biocidal effect Effects 0.000 title description 88
• 150000001875 compounds Chemical class 0.000 claims description 839
• 150000001413 amino acids Chemical class 0.000 claims description 222
• -1 B-alanine Chemical compound 0.000 claims description 187
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 75
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 66
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 208000015181 infectious disease Diseases 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 46
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 45
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 239000004471 Glycine Substances 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 125000005418 aryl aryl group Chemical group 0.000 claims description 34
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 150000005347 biaryls Chemical group 0.000 claims description 32
• 125000001931 aliphatic group Chemical group 0.000 claims description 30
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 239000004472 Lysine Substances 0.000 claims description 28
• FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 28
• 239000004599 antimicrobial Substances 0.000 claims description 25
• 229960004050 aminobenzoic acid Drugs 0.000 claims description 24
• 150000003335 secondary amines Chemical class 0.000 claims description 23
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 22
• 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000006239 protecting group Chemical group 0.000 claims description 22
• JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 claims description 20
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 20
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 20
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 230000000813 microbial effect Effects 0.000 claims description 17
• 108010077895 Sarcosine Proteins 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 14
• 229940043230 sarcosine Drugs 0.000 claims description 14
• XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 12
• SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 12
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• KPDMOOCRWQNXAI-UHFFFAOYSA-N 1,5-diaminocyclohexa-2,4-diene-1-carboxylic acid Chemical compound NC1=CC=CC(N)(C(O)=O)C1 KPDMOOCRWQNXAI-UHFFFAOYSA-N 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 10
• 229910018830 PO3H Inorganic materials 0.000 claims description 8
• 229910006069 SO3H Inorganic materials 0.000 claims description 8
• VJSWHFHHDROXKV-UHFFFAOYSA-N 1,4-diaminocyclohexa-2,4-diene-1-carboxylic acid Chemical compound NC1=CCC(N)(C(O)=O)C=C1 VJSWHFHHDROXKV-UHFFFAOYSA-N 0.000 claims description 7
• XUSKZLBLGHBCLD-UHFFFAOYSA-N 2-(3-aminophenyl)acetic acid Chemical compound NC1=CC=CC(CC(O)=O)=C1 XUSKZLBLGHBCLD-UHFFFAOYSA-N 0.000 claims description 7
• CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 claims description 7
• WOMVICAMAQURRN-UHFFFAOYSA-N 2-(4-aminophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(N)C=C1 WOMVICAMAQURRN-UHFFFAOYSA-N 0.000 claims description 7
• PCNFLKVWBDNNOW-UHFFFAOYSA-N 4-hydrazinylbenzoic acid Chemical compound NNC1=CC=C(C(O)=O)C=C1 PCNFLKVWBDNNOW-UHFFFAOYSA-N 0.000 claims description 7
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 7
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 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
• ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 5
• JOLPMPPNHIACPD-ZZXKWVIFSA-N (e)-3-(4-aminophenyl)prop-2-enoic acid Chemical compound NC1=CC=C(\C=C\C(O)=O)C=C1 JOLPMPPNHIACPD-ZZXKWVIFSA-N 0.000 claims description 4
• 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 4
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• VBYDSMBICNUTKN-UHFFFAOYSA-N 3-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC(C(O)=O)=C1 VBYDSMBICNUTKN-UHFFFAOYSA-N 0.000 claims description 4
• PUWCNJZIFKBDJQ-YFKPBYRVSA-N (3s)-3-azaniumyl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)[C@@H](N)CC(O)=O PUWCNJZIFKBDJQ-YFKPBYRVSA-N 0.000 claims description 3
• SWWBMHIMADRNIK-VKHMYHEASA-N (3s)-3-azaniumyl-4-methoxy-4-oxobutanoate Chemical compound COC(=O)[C@@H]([NH3+])CC([O-])=O SWWBMHIMADRNIK-VKHMYHEASA-N 0.000 claims description 3
• 229940126214 compound 3 Drugs 0.000 claims description 3
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims description 2
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims description 2
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims description 2
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 claims description 2
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• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
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