CA2399640A1 - Selective n-acylation of a82846 glycopeptide analogs - Google Patents
Selective n-acylation of a82846 glycopeptide analogs Download PDFInfo
- Publication number
- CA2399640A1 CA2399640A1 CA002399640A CA2399640A CA2399640A1 CA 2399640 A1 CA2399640 A1 CA 2399640A1 CA 002399640 A CA002399640 A CA 002399640A CA 2399640 A CA2399640 A CA 2399640A CA 2399640 A1 CA2399640 A1 CA 2399640A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- glycopeptide
- formula
- monoacylated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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 58
- 238000005917 acylation reaction Methods 0.000 title description 12
- 238000000034 method Methods 0.000 claims abstract description 45
- 108010015899 Glycopeptides Proteins 0.000 claims abstract description 23
- 102000002068 Glycopeptides Human genes 0.000 claims abstract description 23
- 108010013356 eremomycin Proteins 0.000 claims abstract description 12
- 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 11
- -1 4-(4'-chlorophenyl)benzoyl Chemical group 0.000 claims description 206
- 239000000203 mixture Substances 0.000 claims description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 49
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 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 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 244000005700 microbiome Species 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 241000295644 Staphylococcaceae Species 0.000 claims description 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 208000015181 infectious disease Diseases 0.000 claims description 10
- 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 10
- 230000000845 anti-microbial effect Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 8
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 238000000338 in vitro Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 238000001727 in vivo Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 50
- 230000008569 process Effects 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 125000001072 heteroaryl group Chemical group 0.000 description 40
- 125000003118 aryl group Chemical group 0.000 description 35
- 238000009472 formulation Methods 0.000 description 35
- 125000001424 substituent group Chemical group 0.000 description 34
- 125000004122 cyclic group Chemical group 0.000 description 33
- 239000002253 acid Substances 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 125000006413 ring segment Chemical group 0.000 description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 21
- 125000002252 acyl group Chemical group 0.000 description 21
- 125000000464 thioxo group Chemical group S=* 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 19
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- 125000004434 sulfur atom Chemical group 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 108010059993 Vancomycin Proteins 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000001204 N-oxides Chemical class 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000003242 anti bacterial agent Substances 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229960003165 vancomycin Drugs 0.000 description 11
- 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 11
- 230000010933 acylation Effects 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
- 241000534944 Thia Species 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000006242 amine protecting group Chemical group 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 206010041925 Staphylococcal infections Diseases 0.000 description 7
- 125000003435 aroyl group Chemical group 0.000 description 7
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000012453 solvate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 6
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
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- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- 241000596110 Biosteres Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 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
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 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
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 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
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18168300P | 2000-02-11 | 2000-02-11 | |
| US60/181,683 | 2000-02-11 | ||
| PCT/US2001/004540 WO2001058933A2 (en) | 2000-02-11 | 2001-02-12 | Selective n-acylation of a82846 glycopeptide analogs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2399640A1 true CA2399640A1 (en) | 2001-08-16 |
Family
ID=22665319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002399640A Abandoned CA2399640A1 (en) | 2000-02-11 | 2001-02-12 | Selective n-acylation of a82846 glycopeptide analogs |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7365053B2 (OSRAM) |
| EP (1) | EP1254164B1 (OSRAM) |
| JP (1) | JP2003522197A (OSRAM) |
| KR (1) | KR100796079B1 (OSRAM) |
| CN (1) | CN1422279A (OSRAM) |
| AT (1) | ATE308560T1 (OSRAM) |
| AU (2) | AU2001238180B8 (OSRAM) |
| BR (1) | BR0108268A (OSRAM) |
| CA (1) | CA2399640A1 (OSRAM) |
| CZ (1) | CZ20022722A3 (OSRAM) |
| DE (1) | DE60114567T2 (OSRAM) |
| MX (1) | MXPA02007739A (OSRAM) |
| NO (1) | NO20023761L (OSRAM) |
| NZ (1) | NZ520482A (OSRAM) |
| PL (1) | PL356966A1 (OSRAM) |
| WO (1) | WO2001058933A2 (OSRAM) |
| ZA (1) | ZA200206360B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2497159A1 (en) * | 2002-08-30 | 2004-03-11 | K.U. Leuven Research And Development | Glycopeptide antibiotic and semisynthetic derivatives thereof and their use as antiviral agents |
| 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 |
| GB2577420B (en) | 2017-05-22 | 2022-07-06 | Insmed Inc | Glycopeptide derivative compounds and uses thereof |
| 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 |
| CA2031803C (en) * | 1989-12-13 | 2001-05-29 | Ramakrishnan Nagarajan | Improvements in or relating to glycopeptide deriveratives |
| US5840684A (en) * | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| JP4307723B2 (ja) * | 1998-05-01 | 2009-08-05 | イーライ リリー アンド カンパニー | Ｎ１−修飾グリコペプチド |
-
2001
- 2001-02-12 US US10/203,533 patent/US7365053B2/en not_active Expired - Fee Related
- 2001-02-12 PL PL01356966A patent/PL356966A1/xx not_active Application Discontinuation
- 2001-02-12 CA CA002399640A patent/CA2399640A1/en not_active Abandoned
- 2001-02-12 KR KR1020027010374A patent/KR100796079B1/ko not_active Expired - Fee Related
- 2001-02-12 AT AT01910588T patent/ATE308560T1/de not_active IP Right Cessation
- 2001-02-12 WO PCT/US2001/004540 patent/WO2001058933A2/en not_active Ceased
- 2001-02-12 DE DE60114567T patent/DE60114567T2/de not_active Expired - Lifetime
- 2001-02-12 AU AU2001238180A patent/AU2001238180B8/en not_active Ceased
- 2001-02-12 AU AU3818001A patent/AU3818001A/xx active Pending
- 2001-02-12 NZ NZ520482A patent/NZ520482A/xx unknown
- 2001-02-12 EP EP01910588A patent/EP1254164B1/en not_active Expired - Lifetime
- 2001-02-12 BR BR0108268-0A patent/BR0108268A/pt not_active IP Right Cessation
- 2001-02-12 MX MXPA02007739A patent/MXPA02007739A/es active IP Right Grant
- 2001-02-12 JP JP2001558080A patent/JP2003522197A/ja active Pending
- 2001-02-12 CN CN01807738A patent/CN1422279A/zh 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
Also Published As
| Publication number | Publication date |
|---|---|
| PL356966A1 (en) | 2004-07-12 |
| EP1254164A2 (en) | 2002-11-06 |
| CN1422279A (zh) | 2003-06-04 |
| EP1254164B1 (en) | 2005-11-02 |
| NO20023761D0 (no) | 2002-08-08 |
| AU2001238180B2 (en) | 2005-12-15 |
| AU3818001A (en) | 2001-08-20 |
| MXPA02007739A (es) | 2002-10-11 |
| DE60114567T2 (de) | 2006-07-27 |
| JP2003522197A (ja) | 2003-07-22 |
| AU2001238180B8 (en) | 2006-07-27 |
| US20070219123A1 (en) | 2007-09-20 |
| ATE308560T1 (de) | 2005-11-15 |
| CZ20022722A3 (cs) | 2003-01-15 |
| NZ520482A (en) | 2004-12-24 |
| KR100796079B1 (ko) | 2008-01-21 |
| WO2001058933A3 (en) | 2002-02-14 |
| WO2001058933A2 (en) | 2001-08-16 |
| HK1049171A1 (en) | 2003-05-02 |
| ZA200206360B (en) | 2003-11-10 |
| BR0108268A (pt) | 2003-03-05 |
| NO20023761L (no) | 2002-08-26 |
| DE60114567D1 (de) | 2005-12-08 |
| KR20020073546A (ko) | 2002-09-26 |
| US7365053B2 (en) | 2008-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |