CN1437611A - 糖肽膦酸盐衍生物 - Google Patents
糖肽膦酸盐衍生物 Download PDFInfo
- Publication number
- CN1437611A CN1437611A CN01811350A CN01811350A CN1437611A CN 1437611 A CN1437611 A CN 1437611A CN 01811350 A CN01811350 A CN 01811350A CN 01811350 A CN01811350 A CN 01811350A CN 1437611 A CN1437611 A CN 1437611A
- Authority
- CN
- China
- Prior art keywords
- substituted
- glycopeptide
- group
- alkyl
- hydrogen
- 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.)
- Granted
Links
- 108010015899 Glycopeptides Proteins 0.000 title claims abstract description 119
- 102000002068 Glycopeptides Human genes 0.000 title claims abstract description 119
- -1 Glycopeptide phosphonate derivatives Chemical class 0.000 title claims description 214
- 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 claims abstract description 91
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims abstract description 82
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 152
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 95
- 125000000623 heterocyclic group Chemical group 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 62
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 44
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 42
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000003147 glycosyl group Chemical group 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 27
- 229920000858 Cyclodextrin Polymers 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001118 alkylidene group Chemical group 0.000 claims description 20
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 19
- 239000005864 Sulphur Substances 0.000 claims description 17
- 125000004450 alkenylene group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000012545 processing Methods 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 125000004419 alkynylene group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002337 glycosamines Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 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 3
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 12
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 238000002360 preparation method Methods 0.000 description 56
- 239000002585 base Substances 0.000 description 55
- 108010059993 Vancomycin Proteins 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 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 47
- 229960003165 vancomycin Drugs 0.000 description 46
- 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 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 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 37
- 239000000243 solution Substances 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 29
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000005932 reductive alkylation reaction Methods 0.000 description 19
- 125000003368 amide group Chemical group 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 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 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 150000003573 thiols Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 125000004423 acyloxy group Chemical group 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
- 125000004181 carboxyalkyl group Chemical group 0.000 description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 description 12
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical class NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
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- C07—ORGANIC CHEMISTRY
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- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
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- 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
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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Abstract
Description
化合物 | R3 | R5 | R20 |
1 | 膦酰甲氨基 | H | CH3(CH2)9NHCH2CH2- |
2 | 膦酰甲氨基 | H | CH3(CH2)9OCH2CH2- |
3 | 膦酰甲氨基 | H | CH3(CH2)9SCH2CH2- |
4 | 膦酰甲氨基 | H | CH3(CH2)12- |
5 | 膦酰甲氨基 | H | 4-(4-氯苯基)-苄基 |
6 | 膦酰甲氨基 | H | 2-(4-(4-氯苯基)-苄氨基)乙基 |
7 | 膦酰甲氨基 | H | 4-(4’-氯联苯基)-丁基 |
8 | 膦酰甲氨基 | H | 5-(4’-氯联苯基)-戊基 |
9 | 3-膦酰丙氨基 | H | CH3(CH2)9SCH2CH2- |
10 | 2-羟基-2-膦酰乙氨基 | H | 4-(4-氯苯基)-苄基 |
11 | OH | (膦酰甲基)-氨甲基 | CH3(CH2)9NHCH2CH2- |
12 | OH | (膦酰甲基)-氨甲基 | CH3(CH2)9SCH2CH2- |
13 | OH | (膦酰甲基)-氨甲基 | CH3(CH2)9OCH2CH2- |
14 | OH | (膦酰甲基)-氨甲基 | CH3(CH2)12- |
15 | OH | (膦酰甲基)-氨甲基 | 4-(4-氯苯基)-苄基 |
16 | OH | (膦酰甲基)-氨甲基 | 2-(4-(4-氯苯基)-苄氨基)乙基 |
17 | OH | (膦酰甲基)-氨甲基 | 4-(4’-氯联苯基)-丁基 |
18 | OH | (膦酰甲基)-氨甲基 | 5-(4’-氯联苯基)-戊基 |
19 | OH | (膦酰甲基)-氨甲基 | 3-[4-(4-氯苄氧基)-苄硫基]丙基 |
20 | OH | N-(2-羟基-2-膦酰乙基)氨甲基 | CH3(CH2)9SCH2CH2- |
21 | OH | N-(羧甲基)-N-2-膦酰甲基)-氨甲基 | CH3(CH2)9SCH2CH2- |
22 | OH | N,N-二(膦酰甲基)氨甲基 | CH3(CH2)9NHCH2CH2- |
23 | OH | 3-膦酰丙基-氨甲基 | CH3(CH2)9SCH2CH2- |
24 | OH | 3-膦酰丙基-氨甲基 | 4-(4-氯苯基)-苄基 |
25 | 膦酰甲氨基 | -CH2-N-(N-CH3-D-葡糖胺 | CH3(CH2)9NHCH2CH2- |
26 | OH | (膦酰甲基)-氨甲基 | -(CH2)3NH-SO2-4-(4-氯苯基)苯基 |
化合物编号 | MW(游离碱) | 观察的MH+ |
1 | 1725.63 | 1726.6 |
2 | 1726.62 | 1727.5 |
3 | 1742.68 | 1743.6 |
4 | 1724.64 | 1725.6 |
5 | 1742.96 | 1743.6 |
6 | 1786.03 | 1786.4 |
7 | 1785.04 | 1785.8 |
8 | 1799.07 | 1799.7 |
9 | 1770.74 | 1771.8 |
10 | 1772.99 | 1774.3 |
11 | 1755.66 | 1756.6 |
12 | 1772.71 | 1773.4 |
13 | 1756.64 | 1757.6 |
14 | 1754.67 | 1755.7 |
15 | 1772.99 | 1773.7 |
16 | 1816.06 | 1816.5 |
17 | 1815.01 | 1816.2 |
18 | 1829.10 | 1829.8 |
19 | 1878.1 | 1878.2 |
20 | 1802.74 | 1803.5 |
21 | 1830.75 | 1831.7 |
22 | 1849.66 | 1850.6 |
23 | 1800.76 | 1801.6 |
24 | 1801.04 | 1801.6 |
25 | 1932.86 | 1934.0 |
26 | 1880.12 | 1880.7 |
Claims (34)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US21341000P | 2000-06-22 | 2000-06-22 | |
US60/213,410 | 2000-06-22 |
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CN1437611A true CN1437611A (zh) | 2003-08-20 |
CN100469788C CN100469788C (zh) | 2009-03-18 |
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CNB018113508A Expired - Lifetime CN100469788C (zh) | 2000-06-22 | 2001-05-01 | 糖肽膦酸盐衍生物 |
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US (10) | US6635618B2 (zh) |
EP (1) | EP1292612B1 (zh) |
JP (2) | JP3900491B2 (zh) |
KR (1) | KR100768488B1 (zh) |
CN (1) | CN100469788C (zh) |
AR (1) | AR035333A1 (zh) |
AT (1) | ATE337334T1 (zh) |
AU (2) | AU6110701A (zh) |
BR (1) | BRPI0111222B8 (zh) |
CA (2) | CA2411590C (zh) |
CY (2) | CY1105194T1 (zh) |
CZ (1) | CZ303672B6 (zh) |
DE (2) | DE60122516T2 (zh) |
DK (1) | DK1292612T3 (zh) |
EA (1) | EA005953B1 (zh) |
EG (1) | EG26726A (zh) |
ES (1) | ES2271012T3 (zh) |
HK (1) | HK1052191B (zh) |
HR (1) | HRP20020888B1 (zh) |
HU (2) | HU229370B1 (zh) |
IL (1) | IL152408A (zh) |
IS (1) | IS2303B (zh) |
LU (1) | LU91908I2 (zh) |
MX (1) | MXPA02012745A (zh) |
MY (1) | MY127081A (zh) |
NO (2) | NO330360B1 (zh) |
NZ (1) | NZ522279A (zh) |
PL (1) | PL207101B1 (zh) |
PT (1) | PT1292612E (zh) |
RS (1) | RS50499B (zh) |
SI (1) | SI1292612T1 (zh) |
SK (1) | SK287470B6 (zh) |
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UA (1) | UA75083C2 (zh) |
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