ZA200206360B - Selective N-acylation of A82846 glycopeptide analogs. - Google Patents
Selective N-acylation of A82846 glycopeptide analogs. Download PDFInfo
- Publication number
- ZA200206360B ZA200206360B ZA200206360A ZA200206360A ZA200206360B ZA 200206360 B ZA200206360 B ZA 200206360B ZA 200206360 A ZA200206360 A ZA 200206360A ZA 200206360 A ZA200206360 A ZA 200206360A ZA 200206360 B ZA200206360 B ZA 200206360B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- glycopeptide
- composition
- monoacylated
- substance
- Prior art date
Links
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 title claims abstract description 30
- 230000006181 N-acylation Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 36
- 108010015899 Glycopeptides Proteins 0.000 claims abstract description 16
- 102000002068 Glycopeptides Human genes 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- UECIPBUIMXSXEI-BNSVOVDNSA-N eremomycin Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 UECIPBUIMXSXEI-BNSVOVDNSA-N 0.000 claims abstract description 4
- -1 4-phenylbenzoyl Chemical group 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 244000005700 microbiome Species 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical class O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000000845 anti-microbial effect Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 20
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 241000295644 Staphylococcaceae Species 0.000 claims 6
- 238000000338 in vitro Methods 0.000 claims 4
- 238000001727 in vivo Methods 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 101100289061 Drosophila melanogaster lili gene Proteins 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 24
- 239000002253 acid Substances 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 125000000464 thioxo group Chemical group S=* 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000006242 amine protecting group Chemical group 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 108010059993 Vancomycin Proteins 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229960003165 vancomycin Drugs 0.000 description 5
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009510 drug design Methods 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 241000596110 Biosteres Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000005333 aroyloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- LZJGQIVWUKFTRD-UHFFFAOYSA-N 7-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC2=C1NC=C2 LZJGQIVWUKFTRD-UHFFFAOYSA-N 0.000 description 1
- 102220597425 G0/G1 switch protein 2_M43A_mutation Human genes 0.000 description 1
- 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 description 1
- UVPSSGJTBLNVRE-UHFFFAOYSA-N Moniliformin Natural products O=C1C(OC)=CC(=O)C=2C1=C1C(=O)C(OC)=CC(=O)C1=CC=2 UVPSSGJTBLNVRE-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000002337 glycosamines Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005835 indanylene group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KGPQKNJSZNXOPV-UHFFFAOYSA-N moniliformin Chemical compound OC1=CC(=O)C1=O KGPQKNJSZNXOPV-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18168300P | 2000-02-11 | 2000-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200206360B true ZA200206360B (en) | 2003-11-10 |
Family
ID=22665319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200206360A ZA200206360B (en) | 2000-02-11 | 2002-08-08 | Selective N-acylation of A82846 glycopeptide analogs. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7365053B2 (fr) |
| EP (1) | EP1254164B1 (fr) |
| JP (1) | JP2003522197A (fr) |
| KR (1) | KR100796079B1 (fr) |
| CN (1) | CN1422279A (fr) |
| AT (1) | ATE308560T1 (fr) |
| AU (2) | AU2001238180B8 (fr) |
| BR (1) | BR0108268A (fr) |
| CA (1) | CA2399640A1 (fr) |
| CZ (1) | CZ20022722A3 (fr) |
| DE (1) | DE60114567T2 (fr) |
| HK (1) | HK1049171A1 (fr) |
| MX (1) | MXPA02007739A (fr) |
| NO (1) | NO20023761L (fr) |
| NZ (1) | NZ520482A (fr) |
| PL (1) | PL356966A1 (fr) |
| WO (1) | WO2001058933A2 (fr) |
| ZA (1) | ZA200206360B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050250677A1 (en) * | 2002-08-30 | 2005-11-10 | Jan Balzarini | Glycopeptide antibiotic derivatives |
| US8088387B2 (en) * | 2003-10-10 | 2012-01-03 | Immunogen Inc. | Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates |
| CN1557479A (zh) * | 2004-01-16 | 2004-12-29 | 深圳市海王英特龙生物技术股份有限公 | 干扰素脂质体乳膏 |
| US7632918B2 (en) | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
| WO2018217800A1 (fr) | 2017-05-22 | 2018-11-29 | Insmed Incorporated | Composés dérivés de glycopeptides et leurs utilisations |
| CN108484719A (zh) * | 2018-01-19 | 2018-09-04 | 四川大学 | 硫酸酯化十二指肠糖肽制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4698327A (en) | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4643987A (en) | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| US4639433A (en) | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| NZ236393A (en) | 1989-12-13 | 1992-05-26 | Lilly Co Eli | N-alkylated glycopeptide derivatives prepared from antibiotics a82846 series and pa-42867-a; pharmaceutical compositions |
| US5840684A (en) | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| EP1073447B1 (fr) * | 1998-05-01 | 2007-05-09 | Eli Lilly And Company | Glycopeptides n1-modifies |
-
2001
- 2001-02-12 AU AU2001238180A patent/AU2001238180B8/en not_active Ceased
- 2001-02-12 DE DE60114567T patent/DE60114567T2/de not_active Expired - Lifetime
- 2001-02-12 US US10/203,533 patent/US7365053B2/en not_active Expired - Fee Related
- 2001-02-12 AT AT01910588T patent/ATE308560T1/de not_active IP Right Cessation
- 2001-02-12 MX MXPA02007739A patent/MXPA02007739A/es active IP Right Grant
- 2001-02-12 EP EP01910588A patent/EP1254164B1/fr not_active Expired - Lifetime
- 2001-02-12 CN CN01807738A patent/CN1422279A/zh active Pending
- 2001-02-12 CA CA002399640A patent/CA2399640A1/fr not_active Abandoned
- 2001-02-12 KR KR1020027010374A patent/KR100796079B1/ko not_active IP Right Cessation
- 2001-02-12 BR BR0108268-0A patent/BR0108268A/pt not_active IP Right Cessation
- 2001-02-12 PL PL01356966A patent/PL356966A1/xx not_active Application Discontinuation
- 2001-02-12 WO PCT/US2001/004540 patent/WO2001058933A2/fr active IP Right Grant
- 2001-02-12 NZ NZ520482A patent/NZ520482A/xx unknown
- 2001-02-12 AU AU3818001A patent/AU3818001A/xx active Pending
- 2001-02-12 JP JP2001558080A patent/JP2003522197A/ja active Pending
- 2001-02-12 CZ CZ20022722A patent/CZ20022722A3/cs unknown
-
2002
- 2002-08-08 ZA ZA200206360A patent/ZA200206360B/en unknown
- 2002-08-08 NO NO20023761A patent/NO20023761L/no unknown
-
2003
- 2003-01-02 HK HK03100030A patent/HK1049171A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU3818001A (en) | 2001-08-20 |
| KR20020073546A (ko) | 2002-09-26 |
| KR100796079B1 (ko) | 2008-01-21 |
| NO20023761L (no) | 2002-08-26 |
| CA2399640A1 (fr) | 2001-08-16 |
| US7365053B2 (en) | 2008-04-29 |
| WO2001058933A3 (fr) | 2002-02-14 |
| NZ520482A (en) | 2004-12-24 |
| BR0108268A (pt) | 2003-03-05 |
| DE60114567T2 (de) | 2006-07-27 |
| US20070219123A1 (en) | 2007-09-20 |
| AU2001238180B8 (en) | 2006-07-27 |
| EP1254164A2 (fr) | 2002-11-06 |
| NO20023761D0 (no) | 2002-08-08 |
| AU2001238180B2 (en) | 2005-12-15 |
| CN1422279A (zh) | 2003-06-04 |
| DE60114567D1 (de) | 2005-12-08 |
| HK1049171A1 (en) | 2003-05-02 |
| MXPA02007739A (es) | 2002-10-11 |
| JP2003522197A (ja) | 2003-07-22 |
| PL356966A1 (en) | 2004-07-12 |
| CZ20022722A3 (cs) | 2003-01-15 |
| EP1254164B1 (fr) | 2005-11-02 |
| ATE308560T1 (de) | 2005-11-15 |
| WO2001058933A2 (fr) | 2001-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4927003B2 (ja) | 精製リポペプチドの調製方法 | |
| AU2013356246B2 (en) | Novel depsipeptide and uses thereof | |
| US7868135B2 (en) | Compositions of lipopeptide antibiotic derivatives and methods of use thereof | |
| CN104114547A (zh) | 呫吨酮化合物的衍生物 | |
| EP3606941B1 (fr) | Nouveaux depsipeptides et leurs utilisations | |
| WO2002059145A1 (fr) | Procedes de preparation de lipopeptides purifies | |
| ZA200206360B (en) | Selective N-acylation of A82846 glycopeptide analogs. | |
| EP3111948A1 (fr) | Nouveau lipopeptide bicyclique, préparation et utilisation en tant qu'agent antimicrobien | |
| AU2001238180A1 (en) | Selective N-acylation of A82846 glycopeptide analogs | |
| JP2021510148A (ja) | 新規抗生物質およびその使用方法 | |
| CN118697852A (zh) | 一类达托霉素衍生物的药物用途 | |
| MXPA06000525A (en) | Compositions of lipopeptide antibiotic derivatives and methods of use thereof |