DE69908819T2 - Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten - Google Patents
Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten Download PDFInfo
- Publication number
- DE69908819T2 DE69908819T2 DE69908819T DE69908819T DE69908819T2 DE 69908819 T2 DE69908819 T2 DE 69908819T2 DE 69908819 T DE69908819 T DE 69908819T DE 69908819 T DE69908819 T DE 69908819T DE 69908819 T2 DE69908819 T2 DE 69908819T2
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- group
- alkyl
- hydrogen
- alkenyl
- 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.)
- Expired - Lifetime
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 18
- 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 abstract description 48
- -1 glycopeptide compound Chemical class 0.000 claims description 122
- 239000001257 hydrogen Substances 0.000 claims description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 108010015899 Glycopeptides Proteins 0.000 claims description 36
- 102000002068 Glycopeptides Human genes 0.000 claims description 36
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000004419 alkynylene group Chemical group 0.000 claims description 20
- 125000004450 alkenylene group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- UFYKDFXCZBTLOO-TXICZTDVSA-N 2-amino-2-deoxy-D-gluconic acid Chemical compound [O-]C(=O)[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO UFYKDFXCZBTLOO-TXICZTDVSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000837 carbohydrate group Chemical group 0.000 claims 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- 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 61
- 238000006243 chemical reaction Methods 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- 108010059993 Vancomycin Proteins 0.000 description 51
- 239000000203 mixture Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 47
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin 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@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 47
- 229960003165 vancomycin Drugs 0.000 description 45
- 238000000034 method Methods 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 33
- 235000002639 sodium chloride Nutrition 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- 150000001720 carbohydrates Chemical group 0.000 description 25
- 150000001299 aldehydes Chemical class 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 125000005309 thioalkoxy group Chemical group 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000005932 reductive alkylation reaction Methods 0.000 description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 13
- 230000000844 anti-bacterial effect Effects 0.000 description 13
- 230000001580 bacterial effect Effects 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 13
- 238000004007 reversed phase HPLC Methods 0.000 description 13
- 125000005296 thioaryloxy group Chemical group 0.000 description 13
- 150000003573 thiols Chemical class 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 150000001241 acetals Chemical class 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 125000004442 acylamino group Chemical group 0.000 description 12
- 125000004423 acyloxy group Chemical group 0.000 description 12
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 125000004181 carboxyalkyl group Chemical group 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000005415 substituted alkoxy group Chemical group 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 125000005404 thioheteroaryloxy group Chemical group 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 125000004470 heterocyclooxy group Chemical group 0.000 description 10
- 208000015181 infectious disease Diseases 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 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 9
- 125000000033 alkoxyamino group Chemical group 0.000 description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 9
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 9
- 229960003085 meticillin Drugs 0.000 description 9
- 125000005255 oxyaminoacyl group Chemical group 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 229940088710 antibiotic agent Drugs 0.000 description 8
- 210000002421 cell wall Anatomy 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 229930194542 Keto Natural products 0.000 description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 229960001031 glucose Drugs 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- 125000005323 thioketone group Chemical group 0.000 description 6
- LCTORFDMHNKUSG-XTTLPDOESA-N vancomycin monohydrochloride Chemical compound Cl.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 LCTORFDMHNKUSG-XTTLPDOESA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 241000194031 Enterococcus faecium Species 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 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 5
- 229930182555 Penicillin Natural products 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 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
- 108010053950 Teicoplanin Proteins 0.000 description 5
- OIJZDPGKNVKVBL-UHFFFAOYSA-N Vancosamine Natural products CC1OC(O)CC(C)(N)C1O OIJZDPGKNVKVBL-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 description 5
- 239000008121 dextrose Substances 0.000 description 5
- 150000002016 disaccharides Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 229960001375 lactose Drugs 0.000 description 5
- 231100001225 mammalian toxicity Toxicity 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 229960004793 sucrose Drugs 0.000 description 5
- 229960001608 teicoplanin Drugs 0.000 description 5
- 229960001572 vancomycin hydrochloride Drugs 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
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- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]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])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
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical class N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 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
- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 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
- 229960004559 theobromine Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000008521 threonine Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000006098 transglycosylation Effects 0.000 description 1
- 238000005918 transglycosylation reaction Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11372898P | 1998-12-23 | 1998-12-23 | |
| US113728P | 1998-12-23 | ||
| US12931399P | 1999-04-14 | 1999-04-14 | |
| US129313P | 1999-04-14 | ||
| US16402499P | 1999-11-04 | 1999-11-04 | |
| US164024P | 1999-11-04 | ||
| US16997899P | 1999-12-10 | 1999-12-10 | |
| US169978P | 1999-12-10 | ||
| PCT/US1999/030543 WO2000039156A1 (en) | 1998-12-23 | 1999-12-22 | Glycopeptide derivatives and pharmaceutical compositions containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69908819D1 DE69908819D1 (de) | 2003-07-17 |
| DE69908819T2 true DE69908819T2 (de) | 2004-05-06 |
Family
ID=27493926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69908819T Expired - Lifetime DE69908819T2 (de) | 1998-12-23 | 1999-12-22 | Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten |
Country Status (23)
| Country | Link |
|---|---|
| US (9) | US6392012B1 (https=) |
| EP (1) | EP1140993B1 (https=) |
| JP (1) | JP4362017B2 (https=) |
| KR (1) | KR100665204B1 (https=) |
| CN (1) | CN1249081C (https=) |
| AT (1) | ATE242783T1 (https=) |
| AU (1) | AU768204B2 (https=) |
| BR (1) | BRPI9914221B8 (https=) |
| CA (1) | CA2336445C (https=) |
| CZ (1) | CZ301184B6 (https=) |
| DE (1) | DE69908819T2 (https=) |
| DK (1) | DK1140993T3 (https=) |
| ES (1) | ES2201825T3 (https=) |
| HK (1) | HK1040721B (https=) |
| HU (1) | HU230190B1 (https=) |
| IL (2) | IL140093A0 (https=) |
| NO (1) | NO326066B1 (https=) |
| NZ (1) | NZ508594A (https=) |
| PL (1) | PL198311B1 (https=) |
| PT (1) | PT1140993E (https=) |
| SI (1) | SI1140993T1 (https=) |
| WO (1) | WO2000039156A1 (https=) |
| ZA (1) | ZA200007222B (https=) |
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|---|---|---|---|---|
| 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 |
| US6699836B2 (en) * | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| AU2001238020A1 (en) * | 2000-02-04 | 2001-08-14 | Advanced Medicine, Inc. | Glycopeptide derivatives having antibiotic activity |
| CA2726789A1 (en) | 2000-02-05 | 2001-11-08 | Theravance, Inc. | Cyclodextrin containing glycopeptide antibiotic compositions |
| AU2001259298A1 (en) | 2000-05-02 | 2001-11-12 | Advanced Medicine, Inc. | Polyacid glycopeptide derivatives |
| JP4713810B2 (ja) | 2000-05-02 | 2011-06-29 | セラヴァンス， インコーポレーテッド | グリコペプチドに対する還元的アルキル化プロセス |
| ES2302733T3 (es) * | 2000-06-22 | 2008-08-01 | Theravance, Inc. | Derivados carboxi-sacaridos de glucopeptido. |
| WO2001098329A1 (en) * | 2000-06-22 | 2001-12-27 | Theravance, Inc. | Polyhydroxy glycopeptide derivatives |
| UA75083C2 (uk) | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| US6872804B2 (en) | 2000-06-22 | 2005-03-29 | Theravance, Inc. | Glycopeptide disulfide and thioester derivatives |
| US6905669B2 (en) * | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| TWI275594B (en) * | 2001-08-24 | 2007-03-11 | Theravance Inc | Process for preparing vancomycin phosphonate derivatives |
| TWI312785B (en) * | 2001-08-24 | 2009-08-01 | Theravance Inc | Process for preparing vancomycin derivatives |
| ATE322975T1 (de) | 2001-09-19 | 2006-04-15 | Procter & Gamble | Farbbedruckte mehrschichtstruktur, ein damit hergestellter absorbierender artikel und verfahren zu deren herstellung |
| TWI335332B (en) | 2001-10-12 | 2011-01-01 | Theravance Inc | Cross-linked vancomycin-cephalosporin antibiotics |
| CN101404986B (zh) | 2002-05-17 | 2011-09-28 | 赛奎拉公司 | 用于诊断和治疗感染性疾病的组合物和制药方法 |
| US20040033986A1 (en) | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| TWI325323B (en) * | 2002-05-24 | 2010-06-01 | Theravance Inc | Cross-linked glycopeptide-cephalosporin antibiotics |
| AU2003243574A1 (en) | 2002-06-17 | 2003-12-31 | Theravance, Inc. | PROCESS FOR PREPARING N-PROTECTED Beta-AMINO ALDEHYDE COMPOUNDS |
| BRPI0312654A2 (pt) * | 2002-07-09 | 2017-05-02 | Fasgen Llc | métodos de tratar infecções microbianas em seres humanos e animais |
| MXPA05005338A (es) * | 2002-11-18 | 2005-12-14 | Vicuron Pharm Inc | Metodos para administrar dalbavancin para el tratamiento de infecciones bacterianas. |
| US20060074014A1 (en) * | 2002-11-18 | 2006-04-06 | Vicuron Pharmaceuticals Inc. | Dalbavancin compositions for treatment of bacterial infections |
| JP2007500222A (ja) | 2003-05-23 | 2007-01-11 | セラヴァンス インコーポレーテッド | 架橋グリコペプチド−セファロスポリン抗生物質 |
| DE602004012269T2 (de) * | 2003-07-11 | 2009-04-30 | Theravance, Inc., South San Francisco | Quervernetzte glycopeptid-cephalosporin-antibiotika |
| DE102004055582A1 (de) | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-Heterocyclyl-phthalsäurediamide |
| US8778874B2 (en) | 2004-11-29 | 2014-07-15 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
| US8304597B2 (en) | 2004-12-15 | 2012-11-06 | The Procter And Gamble Company | Method of using an absorbent article having a functional enhancement indicator |
| US7632918B2 (en) * | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US20070185015A1 (en) * | 2005-02-28 | 2007-08-09 | Chiron Corporation and North China Pharmaceutical Corporation | Semi-synthetic desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| JP5178520B2 (ja) | 2005-09-22 | 2013-04-10 | メディバス エルエルシー | 固体ポリマー送達組成物およびその使用法 |
| CA2623198C (en) | 2005-09-22 | 2014-08-05 | Medivas, Llc | Bis-(a-amino)-diol-diester-containing poly(ester amide) and poly(ester urethane) compositions and methods of use |
| WO2007084507A2 (en) * | 2006-01-13 | 2007-07-26 | The Scripps Research Institute | [ψ[CH2NH]PG4] GLYCOPEPTIDE ANTIBIOTIC ANALOGS |
| TW200808818A (en) * | 2006-05-26 | 2008-02-16 | Shionogi & Co | Glycopeptide antibiotic derivatives |
| CA2710602A1 (en) * | 2007-12-26 | 2009-07-09 | Lead Therapeutics, Inc. | Novel semi-synthetic glycopeptides as antibacterial agents |
| CN101959900A (zh) | 2007-12-26 | 2011-01-26 | 盐野义制药株式会社 | 糖肽类抗生素糖基化衍生物 |
| EP2260060A4 (en) | 2008-04-01 | 2013-01-16 | Univ Cornell | ORGANIC SOLUBLE CHITOSA SALT AND CHITOSAN DERIVED BIOMATERIALS MANUFACTURED THEREFROM |
| GB2465863A (en) * | 2008-12-05 | 2010-06-09 | Lead Therapeutics Inc | Semi-synthetic heptapeptidic glycopeptides for the treatment of bacterial infections |
| CN101928330B (zh) * | 2009-06-26 | 2013-10-16 | 上海来益生物药物研究开发中心有限责任公司 | 一种新的化合物及其应用 |
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| KR102237887B1 (ko) | 2013-03-15 | 2021-04-07 | 멜린타 서브시디어리 코프. | 항생제를 사용하여 과체중 및 비만 환자에서 감염을 치료하는 방법 |
| AU2014322817A1 (en) * | 2013-09-23 | 2016-04-21 | Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) | Vancomycin-sugar conjugates and uses thereof |
| WO2016103284A1 (en) * | 2014-12-25 | 2016-06-30 | Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) | Glycopeptides and uses thereof |
| CA3011208A1 (en) * | 2016-01-15 | 2017-07-20 | Universitat Hamburg | Methods for the production of rhamnosylated flavonoids |
| US10696698B2 (en) * | 2016-01-28 | 2020-06-30 | ACatechol, Inc. | Surface primer compositions and methods of use |
| 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 |
| CN107987131B (zh) * | 2017-11-16 | 2021-03-09 | 上海来益生物药物研究开发中心有限责任公司 | 一组具有抗耐药性细菌活性的化合物、其制备方法和应用 |
| CN108409837B (zh) | 2018-03-06 | 2021-09-24 | 上海来益生物药物研究开发中心有限责任公司 | 一组具有抗耐药性细菌活性的糖肽类化合物、其制备方法和应用 |
| NL2023883B1 (en) * | 2019-09-24 | 2021-04-26 | Univ Leiden | Antibiotic compounds |
| CN111620931B (zh) * | 2020-06-12 | 2021-12-17 | 苏州博源医疗科技有限公司 | 万古霉素衍生物及其制备方法和应用 |
| CN114213284B (zh) * | 2022-01-04 | 2023-08-01 | 丽珠集团福州福兴医药有限公司 | (9h-芴-9-基)-癸基(2-氧代乙基)氨基甲酸甲酯及其合成方法 |
| CN121270649A (zh) * | 2024-07-03 | 2026-01-06 | 烟台新药创制山东省实验室 | 一类万古霉素衍生物、其制备方法、药物组合物和用途 |
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| PT1140993E (pt) * | 1998-12-23 | 2003-10-31 | Theravance Inc | Derivados de glicopeptidos e composicoes farmaceuticas contendo os mesmos |
| UA75083C2 (uk) | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| TWI325323B (en) | 2002-05-24 | 2010-06-01 | Theravance Inc | Cross-linked glycopeptide-cephalosporin antibiotics |
| DE602004012269T2 (de) | 2003-07-11 | 2009-04-30 | Theravance, Inc., South San Francisco | Quervernetzte glycopeptid-cephalosporin-antibiotika |
-
1999
- 1999-12-22 PT PT99965331T patent/PT1140993E/pt unknown
- 1999-12-22 WO PCT/US1999/030543 patent/WO2000039156A1/en not_active Ceased
- 1999-12-22 DE DE69908819T patent/DE69908819T2/de not_active Expired - Lifetime
- 1999-12-22 CA CA2336445A patent/CA2336445C/en not_active Expired - Lifetime
- 1999-12-22 US US09/470,209 patent/US6392012B1/en not_active Expired - Lifetime
- 1999-12-22 HK HK02102171.5A patent/HK1040721B/en unknown
- 1999-12-22 KR KR1020017003918A patent/KR100665204B1/ko not_active Expired - Lifetime
- 1999-12-22 BR BRPI9914221A patent/BRPI9914221B8/pt not_active IP Right Cessation
- 1999-12-22 HU HU0400887A patent/HU230190B1/hu unknown
- 1999-12-22 CZ CZ20010022A patent/CZ301184B6/cs not_active IP Right Cessation
- 1999-12-22 JP JP2000591067A patent/JP4362017B2/ja not_active Expired - Fee Related
- 1999-12-22 DK DK99965331T patent/DK1140993T3/da active
- 1999-12-22 EP EP99965331A patent/EP1140993B1/en not_active Expired - Lifetime
- 1999-12-22 CN CNB99809434XA patent/CN1249081C/zh not_active Expired - Lifetime
- 1999-12-22 SI SI9930389T patent/SI1140993T1/xx unknown
- 1999-12-22 PL PL348451A patent/PL198311B1/pl unknown
- 1999-12-22 ES ES99965331T patent/ES2201825T3/es not_active Expired - Lifetime
- 1999-12-22 AT AT99965331T patent/ATE242783T1/de active
- 1999-12-22 AU AU31273/00A patent/AU768204B2/en not_active Expired
- 1999-12-22 IL IL14009399A patent/IL140093A0/xx active IP Right Grant
- 1999-12-22 NZ NZ508594A patent/NZ508594A/en not_active IP Right Cessation
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2000
- 2000-09-06 US US09/656,473 patent/US6444786B1/en not_active Expired - Lifetime
- 2000-11-01 US US09/674,456 patent/US6455669B1/en not_active Expired - Lifetime
- 2000-12-05 IL IL140093A patent/IL140093A/en not_active IP Right Cessation
- 2000-12-06 ZA ZA200007222A patent/ZA200007222B/xx unknown
- 2000-12-12 NO NO20006323A patent/NO326066B1/no not_active IP Right Cessation
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2002
- 2002-03-06 US US10/092,088 patent/US6962970B2/en not_active Expired - Lifetime
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2004
- 2004-04-15 US US10/825,038 patent/US6949681B2/en not_active Expired - Lifetime
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2005
- 2005-05-13 US US11/128,901 patent/US7101964B2/en not_active Expired - Lifetime
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2006
- 2006-04-17 US US11/405,234 patent/US7351791B2/en not_active Expired - Fee Related
-
2007
- 2007-10-24 US US11/977,377 patent/US7723470B2/en not_active Expired - Fee Related
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2009
- 2009-05-08 US US12/437,778 patent/US8030445B2/en not_active Expired - Fee Related
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