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
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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
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- 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)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (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 (enExample) | 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 (enExample) |
| EP (1) | EP2373694A1 (enExample) |
| JP (1) | JP2012510999A (enExample) |
| KR (1) | KR20110099028A (enExample) |
| CN (1) | CN102307903A (enExample) |
| AR (1) | AR075354A1 (enExample) |
| AU (1) | AU2009322925A1 (enExample) |
| CA (1) | CA2745446A1 (enExample) |
| GB (1) | GB2465863A (enExample) |
| IL (1) | IL213390A0 (enExample) |
| TW (1) | TW201021805A (enExample) |
| WO (1) | WO2010065174A1 (enExample) |
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 |
| IL270685B (en) * | 2017-05-22 | 2022-09-01 | Insmed Inc | Cleavable derivatives of lipoglycopeptide and their uses |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2337103A1 (en) * | 1998-07-14 | 2000-01-27 | Robert Kerns | Glycopeptide antibiotics, combinatorial libraries of glycopeptide antibiotics and methods of producing same |
| PT1140993E (pt) * | 1998-12-23 | 2003-10-31 | Theravance Inc | Derivados de glicopeptidos e composicoes farmaceuticas contendo os mesmos |
| US6518243B1 (en) * | 1999-04-02 | 2003-02-11 | Trustees Of Princeton University | Desleucyl glycopeptide antibiotics and methods of making same |
| CN1425025A (zh) * | 1999-12-15 | 2003-06-18 | 卡比斯特制药公司 | 作为抗菌剂的新颖的脂肽 |
| US6397405B1 (en) * | 2000-04-11 | 2002-06-04 | Thetford Corporation | Flush toilet for RV's and boats |
| AU2001259298A1 (en) * | 2000-05-02 | 2001-11-12 | Advanced Medicine, Inc. | Polyacid glycopeptide derivatives |
| UA75083C2 (uk) * | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| ES2302733T3 (es) * | 2000-06-22 | 2008-08-01 | Theravance, Inc. | Derivados carboxi-sacaridos de glucopeptido. |
| 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 |
| JP2006528704A (ja) * | 2003-05-27 | 2006-12-21 | セラヴァンス インコーポレーテッド | グリコペプチド抗細菌剤と組み合わせたポリエンマクロライド抗真菌剤の使用 |
| US8778874B2 (en) * | 2004-11-29 | 2014-07-15 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
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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 EP EP09830765A patent/EP2373694A1/en not_active Withdrawn
- 2009-09-01 CA CA2745446A patent/CA2745446A1/en not_active Abandoned
- 2009-09-01 US US12/552,221 patent/US20110015119A1/en not_active Abandoned
- 2009-09-01 KR KR1020117015395A patent/KR20110099028A/ko not_active Withdrawn
- 2009-09-01 JP JP2011539532A patent/JP2012510999A/ja active Pending
- 2009-09-01 WO PCT/US2009/055633 patent/WO2010065174A1/en not_active Ceased
- 2009-09-01 CN CN2009801561496A patent/CN102307903A/zh active Pending
- 2009-09-02 TW TW098129618A patent/TW201021805A/zh unknown
- 2009-09-02 AR ARP090103380A patent/AR075354A1/es not_active Application Discontinuation
-
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 |
| US20110015119A1 (en) | 2011-01-20 |
| CA2745446A1 (en) | 2010-06-10 |
| WO2010065174A1 (en) | 2010-06-10 |
| EP2373694A1 (en) | 2011-10-12 |
| KR20110099028A (ko) | 2011-09-05 |
| GB2465863A (en) | 2010-06-09 |
| CN102307903A (zh) | 2012-01-04 |
| IL213390A0 (en) | 2011-07-31 |
| GB0915258D0 (en) | 2009-10-07 |
| TW201021805A (en) | 2010-06-16 |
| AR075354A1 (es) | 2011-03-30 |
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