JP2012510999A - 抗菌薬としての新規の半合成糖ペプチド - Google Patents
抗菌薬としての新規の半合成糖ペプチド Download PDFInfo
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- JP2012510999A JP2012510999A JP2011539532A JP2011539532A JP2012510999A JP 2012510999 A JP2012510999 A JP 2012510999A JP 2011539532 A JP2011539532 A JP 2011539532A JP 2011539532 A JP2011539532 A JP 2011539532A JP 2012510999 A JP2012510999 A JP 2012510999A
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- Prior art keywords
- alkyl
- alkoxy
- substituted
- resistant
- bacteria
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- 108010015899 Glycopeptides Proteins 0.000 title abstract description 27
- 102000002068 Glycopeptides Human genes 0.000 title abstract description 27
- 239000003242 anti bacterial agent Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 648
- 238000000034 method Methods 0.000 claims abstract description 179
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 116
- 150000001413 amino acids Chemical class 0.000 claims abstract description 26
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 19
- 235000000346 sugar Nutrition 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 125000002252 acyl group Chemical group 0.000 claims abstract description 11
- 150000001408 amides Chemical class 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 8
- 150000002678 macrocyclic compounds Chemical class 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 226
- 239000001257 hydrogen Substances 0.000 claims description 225
- 125000000217 alkyl group Chemical group 0.000 claims description 223
- 150000003839 salts Chemical class 0.000 claims description 209
- 150000002148 esters Chemical class 0.000 claims description 204
- 239000012453 solvate Substances 0.000 claims description 203
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 200
- 229940002612 prodrug Drugs 0.000 claims description 186
- 239000000651 prodrug Substances 0.000 claims description 186
- 125000001072 heteroaryl group Chemical group 0.000 claims description 156
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 136
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 229910052736 halogen Inorganic materials 0.000 claims description 95
- 150000002367 halogens Chemical class 0.000 claims description 95
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 86
- 150000002431 hydrogen Chemical class 0.000 claims description 83
- 229910052799 carbon Inorganic materials 0.000 claims description 78
- 125000003107 substituted aryl group Chemical group 0.000 claims description 65
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 125000004429 atom Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 34
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 150000003138 primary alcohols Chemical class 0.000 claims description 12
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 11
- 125000005418 aryl aryl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
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- 238000010511 deprotection reaction Methods 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000006352 cycloaddition reaction Methods 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 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 compound 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 abstract description 14
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 9
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract description 9
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 208000010753 nasal discharge Diseases 0.000 description 1
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- 239000007922 nasal spray Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
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- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 239000000668 oral spray Substances 0.000 description 1
- 229940041678 oral spray Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 229940098956 topical powder Drugs 0.000 description 1
- 229940041677 topical spray Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 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
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2008/085716 WO2009085562A1 (en) | 2007-12-26 | 2008-12-05 | Novel semi-synthetic glycopeptides as antibacterial agents |
| USPCT/US2008/085716 | 2008-12-05 | ||
| US22016709P | 2009-06-24 | 2009-06-24 | |
| US61/220,167 | 2009-06-24 | ||
| PCT/US2009/055633 WO2010065174A1 (en) | 2008-12-05 | 2009-09-01 | Novel semi-synthetic glycopeptides as antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012510999A true JP2012510999A (ja) | 2012-05-17 |
| JP2012510999A5 JP2012510999A5 (https=) | 2012-11-01 |
Family
ID=41203726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011539532A Pending JP2012510999A (ja) | 2008-12-05 | 2009-09-01 | 抗菌薬としての新規の半合成糖ペプチド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20110015119A1 (https=) |
| EP (1) | EP2373694A1 (https=) |
| JP (1) | JP2012510999A (https=) |
| KR (1) | KR20110099028A (https=) |
| CN (1) | CN102307903A (https=) |
| AR (1) | AR075354A1 (https=) |
| AU (1) | AU2009322925A1 (https=) |
| CA (1) | CA2745446A1 (https=) |
| GB (1) | GB2465863A (https=) |
| IL (1) | IL213390A0 (https=) |
| TW (1) | TW201021805A (https=) |
| WO (1) | WO2010065174A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011140009A1 (en) * | 2010-05-04 | 2011-11-10 | Biomarin Pharmaceutical Inc. | Methods of using semi-synthetic glycopeptides as antibacterial agents |
| CN107325159A (zh) | 2016-04-29 | 2017-11-07 | 中国科学院上海药物研究所 | 一类万古霉素衍生物、其制备方法、药物组合物和用途 |
| GB2577420B (en) | 2017-05-22 | 2022-07-06 | Insmed Inc | Glycopeptide derivative compounds and uses thereof |
| CN109422800A (zh) * | 2017-08-22 | 2019-03-05 | 复旦大学 | 抗革兰氏阳性菌季铵盐糖肽类化合物及其药用用途 |
| CN111793076B (zh) * | 2020-06-05 | 2021-10-12 | 华北制药河北华民药业有限责任公司 | 一种注射用硫酸头孢匹罗的制备方法 |
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| JP2008531702A (ja) * | 2005-02-28 | 2008-08-14 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス， インコーポレイテッド | 抗菌活性を有する半合成グリコペプチド |
| JP2008531713A (ja) * | 2005-02-28 | 2008-08-14 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス， インコーポレイテッド | 抗菌活性を有する、半合成デスメチル−バンコマイシンベースのグリコペプチド |
| WO2008140973A1 (en) * | 2007-05-08 | 2008-11-20 | Lead Therapeutics, Inc. | Semi-synthetic glycopeptides with antibacterial activity |
| JP2011507959A (ja) * | 2007-12-26 | 2011-03-10 | レアド トヘラペウトイクス，インコーポレーテッド | 抗菌薬としての新規半合成糖ペプチド |
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| JPH0662674B2 (ja) * | 1985-01-11 | 1994-08-17 | 三共株式会社 | 抗生物質クロロポリスポリンｂまたはｃ |
| US4643987A (en) * | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| NZ509165A (en) * | 1998-07-14 | 2003-08-29 | Univ Princeton | Glycopeptide antobiotics, combinatorial libraries of glycopeptide antibiotics and methods of producing same |
| DE69908819T2 (de) * | 1998-12-23 | 2004-05-06 | Theravance, Inc., South San Francisco | Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten |
| AU4054900A (en) * | 1999-04-02 | 2000-10-23 | Advanced Medicine East, Inc. | Desleucyl glycopeptide antibiotics and methods of making same |
| MXPA02006029A (es) * | 1999-12-15 | 2004-08-23 | Cubist Pharm Inc | Lipopeptidos novedosos como agentes antibacterianos. |
| US6397405B1 (en) * | 2000-04-11 | 2002-06-04 | Thetford Corporation | Flush toilet for RV's and boats |
| US6770621B2 (en) * | 2000-05-02 | 2004-08-03 | Theravance, Inc. | Polyacid glycopeptide derivatives |
| UA75083C2 (uk) * | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| US6620781B2 (en) * | 2000-06-22 | 2003-09-16 | Theravance, Inc. | Glycopeptide carboxy-saccharide derivatives |
| US20030008812A1 (en) * | 2001-02-02 | 2003-01-09 | Christensen Burton G. | Glycopeptide derivatives |
| TWI233932B (en) * | 2001-08-24 | 2005-06-11 | Theravance Inc | Process for purifying glycopeptide phosphonate derivatives |
| US7521418B2 (en) * | 2003-05-27 | 2009-04-21 | Theravance, Inc. | Use of a polyene macrolide antifungal agent in combination with a glycopeptide antibacterial agent |
| CA2588285A1 (en) * | 2004-11-29 | 2006-06-01 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
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| WO2008075684A1 (ja) * | 2006-12-19 | 2008-06-26 | Shionogi & Co., Ltd. | グリコペプチド抗生物質誘導体 |
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| US20100216699A1 (en) * | 2009-02-09 | 2010-08-26 | Lead Therapeutics, Inc. | Semi-synthetic glycopeptides having antibacterial activity |
-
2008
- 2008-12-05 GB GB0915258A patent/GB2465863A/en not_active Withdrawn
-
2009
- 2009-09-01 AU AU2009322925A patent/AU2009322925A1/en not_active Abandoned
- 2009-09-01 CA CA2745446A patent/CA2745446A1/en not_active Abandoned
- 2009-09-01 CN CN2009801561496A patent/CN102307903A/zh active Pending
- 2009-09-01 KR KR1020117015395A patent/KR20110099028A/ko not_active Withdrawn
- 2009-09-01 US US12/552,221 patent/US20110015119A1/en not_active Abandoned
- 2009-09-01 EP EP09830765A patent/EP2373694A1/en not_active Withdrawn
- 2009-09-01 WO PCT/US2009/055633 patent/WO2010065174A1/en not_active Ceased
- 2009-09-01 JP JP2011539532A patent/JP2012510999A/ja active Pending
- 2009-09-02 AR ARP090103380A patent/AR075354A1/es not_active Application Discontinuation
- 2009-09-02 TW TW098129618A patent/TW201021805A/zh unknown
-
2011
- 2011-06-05 IL IL213390A patent/IL213390A0/en unknown
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| JP2008531702A (ja) * | 2005-02-28 | 2008-08-14 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス， インコーポレイテッド | 抗菌活性を有する半合成グリコペプチド |
| JP2008531713A (ja) * | 2005-02-28 | 2008-08-14 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス， インコーポレイテッド | 抗菌活性を有する、半合成デスメチル−バンコマイシンベースのグリコペプチド |
| WO2008140973A1 (en) * | 2007-05-08 | 2008-11-20 | Lead Therapeutics, Inc. | Semi-synthetic glycopeptides with antibacterial activity |
| JP2011507959A (ja) * | 2007-12-26 | 2011-03-10 | レアド トヘラペウトイクス，インコーポレーテッド | 抗菌薬としての新規半合成糖ペプチド |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009322925A1 (en) | 2011-06-30 |
| GB0915258D0 (en) | 2009-10-07 |
| KR20110099028A (ko) | 2011-09-05 |
| CA2745446A1 (en) | 2010-06-10 |
| AR075354A1 (es) | 2011-03-30 |
| US20110015119A1 (en) | 2011-01-20 |
| GB2465863A (en) | 2010-06-09 |
| IL213390A0 (en) | 2011-07-31 |
| TW201021805A (en) | 2010-06-16 |
| EP2373694A1 (en) | 2011-10-12 |
| WO2010065174A1 (en) | 2010-06-10 |
| CN102307903A (zh) | 2012-01-04 |
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