MX2012011453A - Compuestos de tetraciclina policíclica. - Google Patents
Compuestos de tetraciclina policíclica.Info
- Publication number
- MX2012011453A MX2012011453A MX2012011453A MX2012011453A MX2012011453A MX 2012011453 A MX2012011453 A MX 2012011453A MX 2012011453 A MX2012011453 A MX 2012011453A MX 2012011453 A MX2012011453 A MX 2012011453A MX 2012011453 A MX2012011453 A MX 2012011453A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- compound
- heterocyclyl
- alkylene
- ring
- Prior art date
Links
- -1 Polycyclic tetracycline compounds Chemical class 0.000 title claims description 80
- 239000004098 Tetracycline Substances 0.000 title claims description 79
- 235000019364 tetracycline Nutrition 0.000 title claims description 79
- 229960002180 tetracycline Drugs 0.000 title claims description 76
- 229930101283 tetracycline Natural products 0.000 title claims description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 447
- 150000003839 salts Chemical class 0.000 claims abstract description 61
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 208000015181 infectious disease Diseases 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 78
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 150000003522 tetracyclines Chemical class 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims description 33
- 230000001154 acute effect Effects 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 239000000460 chlorine Chemical group 0.000 claims description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 241000894006 Bacteria Species 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- SOVUOXKZCCAWOJ-HJYUBDRYSA-N (4s,4as,5ar,12ar)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O SOVUOXKZCCAWOJ-HJYUBDRYSA-N 0.000 claims description 12
- 208000035143 Bacterial infection Diseases 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 229960004089 tigecycline Drugs 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 11
- 241000606768 Haemophilus influenzae Species 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 239000003242 anti bacterial agent Substances 0.000 claims description 9
- 229940088710 antibiotic agent Drugs 0.000 claims description 9
- 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 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 108010059993 Vancomycin Proteins 0.000 claims description 8
- 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 claims description 8
- 229960003165 vancomycin Drugs 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 241000894007 species Species 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 6
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 241001156739 Actinobacteria <phylum> Species 0.000 claims description 5
- 241000194032 Enterococcus faecalis Species 0.000 claims description 5
- 241000194031 Enterococcus faecium Species 0.000 claims description 5
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 5
- 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 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 229960003085 meticillin Drugs 0.000 claims description 5
- 206010040872 skin infection Diseases 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 241000589291 Acinetobacter Species 0.000 claims description 4
- 108700042778 Antimicrobial Peptides Proteins 0.000 claims description 4
- 102000044503 Antimicrobial Peptides Human genes 0.000 claims description 4
- 241000589248 Legionella Species 0.000 claims description 4
- 241000194017 Streptococcus Species 0.000 claims description 4
- 241000193985 Streptococcus agalactiae Species 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims description 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
- 241000304886 Bacilli Species 0.000 claims description 3
- 241001112696 Clostridia Species 0.000 claims description 3
- 241000194033 Enterococcus Species 0.000 claims description 3
- 241000589989 Helicobacter Species 0.000 claims description 3
- 241000589242 Legionella pneumophila Species 0.000 claims description 3
- 208000016604 Lyme disease Diseases 0.000 claims description 3
- 241001430197 Mollicutes Species 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 241000204031 Mycoplasma Species 0.000 claims description 3
- 241000191940 Staphylococcus Species 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 229940115932 legionella pneumophila Drugs 0.000 claims description 3
- 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 150000003952 β-lactams Chemical class 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 201000001178 Bacterial Pneumonia Diseases 0.000 claims description 2
- 241000605059 Bacteroidetes Species 0.000 claims description 2
- 241000589968 Borrelia Species 0.000 claims description 2
- 241000589876 Campylobacter Species 0.000 claims description 2
- 241001185363 Chlamydiae Species 0.000 claims description 2
- 241000498849 Chlamydiales Species 0.000 claims description 2
- 241000193403 Clostridium Species 0.000 claims description 2
- 241000186216 Corynebacterium Species 0.000 claims description 2
- 241000186781 Listeria Species 0.000 claims description 2
- 241000589289 Moraxellaceae Species 0.000 claims description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 2
- 241000202934 Mycoplasma pneumoniae Species 0.000 claims description 2
- 241000588656 Neisseriaceae Species 0.000 claims description 2
- 241000187654 Nocardia Species 0.000 claims description 2
- 241000606752 Pasteurellaceae Species 0.000 claims description 2
- 241000186429 Propionibacterium Species 0.000 claims description 2
- 241000947836 Pseudomonadaceae Species 0.000 claims description 2
- 241000606651 Rickettsiales Species 0.000 claims description 2
- 241000589886 Treponema Species 0.000 claims description 2
- 241000607493 Vibrionaceae Species 0.000 claims description 2
- 229960000106 biosimilars Drugs 0.000 claims description 2
- 229940124307 fluoroquinolone Drugs 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229940072172 tetracycline antibiotic Drugs 0.000 claims description 2
- 229940041010 fourth-generation cephalosporins Drugs 0.000 claims 1
- 229940041008 second-generation cephalosporins Drugs 0.000 claims 1
- 229940041007 third-generation cephalosporins Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 350
- 238000005481 NMR spectroscopy Methods 0.000 description 189
- 239000000243 solution Substances 0.000 description 183
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 171
- 235000019439 ethyl acetate Nutrition 0.000 description 159
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 133
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 122
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
- 239000011541 reaction mixture Substances 0.000 description 101
- 230000002829 reductive effect Effects 0.000 description 101
- 230000015572 biosynthetic process Effects 0.000 description 92
- 238000003786 synthesis reaction Methods 0.000 description 90
- 239000000203 mixture Substances 0.000 description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- 229910001868 water Inorganic materials 0.000 description 78
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 72
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 65
- 239000007787 solid Substances 0.000 description 65
- 229910052938 sodium sulfate Inorganic materials 0.000 description 62
- 235000011152 sodium sulphate Nutrition 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 47
- 229920006395 saturated elastomer Polymers 0.000 description 45
- 239000012267 brine Substances 0.000 description 43
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
- 239000007832 Na2SO4 Substances 0.000 description 40
- 208000035475 disorder Diseases 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- 239000012044 organic layer Substances 0.000 description 34
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- 201000010099 disease Diseases 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 31
- 238000003818 flash chromatography Methods 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 239000007864 aqueous solution Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 25
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 24
- 210000004072 lung Anatomy 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 23
- 229960000484 ceftazidime Drugs 0.000 description 23
- 238000000746 purification Methods 0.000 description 23
- 239000010779 crude oil Substances 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 22
- 235000017557 sodium bicarbonate Nutrition 0.000 description 22
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 22
- 230000001684 chronic effect Effects 0.000 description 21
- 239000006196 drop Substances 0.000 description 21
- 239000000284 extract Substances 0.000 description 21
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000001580 bacterial effect Effects 0.000 description 18
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 229960003376 levofloxacin Drugs 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 206010028980 Neoplasm Diseases 0.000 description 16
- 229960002770 ertapenem Drugs 0.000 description 16
- 230000009467 reduction Effects 0.000 description 16
- 229960003907 linezolid Drugs 0.000 description 15
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 210000000988 bone and bone Anatomy 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 108010078777 Colistin Proteins 0.000 description 13
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 13
- 229930182566 Gentamicin Natural products 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- 125000002619 bicyclic group Chemical group 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 229960003346 colistin Drugs 0.000 description 13
- 229960002518 gentamicin Drugs 0.000 description 13
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 description 13
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 13
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 13
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pulmonology (AREA)
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- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Purification Treatments By Anaerobic Or Anaerobic And Aerobic Bacteria Or Animals (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| PCT/US2011/030532 WO2011123536A1 (en) | 2010-03-31 | 2011-03-30 | Polycyclic tetracycline compounds |
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| MX2012011453A true MX2012011453A (es) | 2013-02-15 |
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| US7607243B2 (en) | 2006-05-03 | 2009-10-27 | Nike, Inc. | Athletic or other performance sensing systems |
| CA2761241C (en) | 2009-05-08 | 2018-02-27 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| US9624166B2 (en) | 2009-08-28 | 2017-04-18 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| KR101879751B1 (ko) | 2010-03-31 | 2018-08-16 | 테트라페이즈 파마슈티컬스, 인코포레이티드 | 폴리사이클릭 테트라사이클린 화합물 |
| HUE042600T2 (hu) | 2012-08-31 | 2019-07-29 | Tetraphase Pharmaceuticals Inc | Tetraciklin vegyületek |
| US9580758B2 (en) | 2013-11-12 | 2017-02-28 | Luc Montagnier | System and method for the detection and treatment of infection by a microbial agent associated with HIV infection |
| MA40836A (fr) * | 2014-10-23 | 2017-08-29 | Tetraphase Pharmaceuticals Inc | Procédures de semi-synthèse |
| SG11201901390TA (en) * | 2016-08-30 | 2019-03-28 | Tetraphase Pharmaceuticals Inc | Tetracycline compounds and methods of treatment |
| EP3529236B1 (en) | 2016-10-19 | 2024-02-07 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
| US20220401457A1 (en) * | 2019-08-30 | 2022-12-22 | Emory University | Use of Deoxycholic Acid, Derivatives, or Salts Thereof in Managing Bacterial Infections and Compositions Related Thereto |
| WO2021207217A1 (en) * | 2020-04-06 | 2021-10-14 | University Of Virginia Patent Foundation | Compositions and methods for treating viruses |
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| US3304227A (en) | 1965-07-15 | 1967-02-14 | Loyal E Loveless | Antibiotic-containing animal feed |
| US4704383A (en) | 1983-12-29 | 1987-11-03 | The Research Foundation Of State University Of New York | Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same |
| US4666897A (en) | 1983-12-29 | 1987-05-19 | Research Foundation Of State University | Inhibition of mammalian collagenolytic enzymes by tetracyclines |
| US4925833A (en) | 1983-12-29 | 1990-05-15 | The Research Foundation Of State University Of New York | Use of tetracycline to enhance bone protein synthesis and/or treatment of osteoporosis |
| USRE34656E (en) | 1983-12-29 | 1994-07-05 | The Research Foundation Of State University Of New York | Use of tetracycline to enhance bone protein synthesis and/or treatment of bone deficiency |
| US4935412A (en) | 1983-12-29 | 1990-06-19 | The Research Foundation Of State University Of New York | Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same |
| JP3016587B2 (ja) | 1989-12-04 | 2000-03-06 | ザ・リサーチ・ファンデーション・オブ・ステート・ユニバーシティ・オブ・ニューヨーク | 非ステロイド抗炎症剤及びテトラサイクリンの配合 |
| US5308839A (en) | 1989-12-04 | 1994-05-03 | The Research Foundation Of State University Of New York | Composition comprising non-steroidal anti-inflammatory agent tenidap and effectively non-antibacterial tetracycline |
| US5770588A (en) | 1991-02-11 | 1998-06-23 | The Research Foundation Of State University Of New York | Non-antibacterial tetracycline compositions of the prevention and treatment of root caries |
| US5231017A (en) | 1991-05-17 | 1993-07-27 | Solvay Enzymes, Inc. | Process for producing ethanol |
| US5258371A (en) | 1992-05-29 | 1993-11-02 | Kuraray Co., Ltd. | Method to reduce connective tissue destruction |
| US6043225A (en) | 1992-06-12 | 2000-03-28 | Board Of Regents Of The University Of Washington | Diagnosis and treatment of arterial chlamydial granuloma |
| DK0599397T3 (da) | 1992-11-17 | 1996-09-16 | Univ New York State Res Found | Tetracycliner, herunder non-mikrobielle, kemisk-modificerede tetracycliner, inhiberer overdreven collagentværbinding ved diabetes |
| US5523297A (en) | 1993-03-02 | 1996-06-04 | The Research Foundation Of State University Of New York | Inhibition of excessive phospholipase A2 activity and/or production by non-antimicrobial tetracyclines |
| US6043231A (en) | 1993-03-02 | 2000-03-28 | The Research Foundation Of State Univ. Of New York | Inhibition of excessive phospholipase A2 activity and/or production by non-antimicrobial tetracyclines |
| US5668122A (en) | 1993-07-28 | 1997-09-16 | Fife; Rose S. | Method to treat cancer with tetracyclines |
| WO1995022529A1 (en) | 1994-02-17 | 1995-08-24 | Pfizer Inc. | 9-(substituted amino)-alpha-6-deoxy-5-oxy tetracycline derivatives, their preparation and their use as antibiotics |
| US5843925A (en) | 1994-12-13 | 1998-12-01 | American Cyanamid Company | Methods for inhibiting angiogenesis, proliferation of endothelial or tumor cells and tumor growth |
| US5834449A (en) | 1996-06-13 | 1998-11-10 | The Research Foundation Of State University Of New York | Treatment of aortic and vascular aneurysms with tetracycline compounds |
| US5827840A (en) | 1996-08-01 | 1998-10-27 | The Research Foundation Of State University Of New York | Promotion of wound healing by chemically-modified tetracyclines |
| US5789395A (en) | 1996-08-30 | 1998-08-04 | The Research Foundation Of State University Of New York | Method of using tetracycline compounds for inhibition of endogenous nitric oxide production |
| US5919774A (en) | 1996-12-10 | 1999-07-06 | Eli Lilly And Company | Pyrroles as sPLA2 inhibitors |
| US5837696A (en) | 1997-01-15 | 1998-11-17 | The Research Foundation Of State University Of New York | Method of inhibiting cancer growth |
| US5773430A (en) | 1997-03-13 | 1998-06-30 | Research Foundation Of State University Of New York | Serine proteinase inhibitory activity by hydrophobic tetracycline |
| US5929055A (en) | 1997-06-23 | 1999-07-27 | The Research Foundation Of State University Of New York | Therapeutic method for management of diabetes mellitus |
| US6277061B1 (en) | 1998-03-31 | 2001-08-21 | The Research Foundation Of State University Of New York | Method of inhibiting membrane-type matrix metalloproteinase |
| US6015804A (en) | 1998-09-11 | 2000-01-18 | The Research Foundation Of State University Of New York | Method of using tetracycline compounds to enhance interleukin-10 production |
| US5977091A (en) | 1998-09-21 | 1999-11-02 | The Research Foundation Of State University Of New York | Method of preventing acute lung injury |
| US5998390A (en) | 1998-09-28 | 1999-12-07 | The Research Foundation Of State University Of New York | Combination of bisphosphonate and tetracycline |
| US6231894B1 (en) | 1999-10-21 | 2001-05-15 | Duke University | Treatments based on discovery that nitric oxide synthase is a paraquat diaphorase |
| CN103214409B (zh) * | 2004-05-21 | 2015-10-21 | 哈佛大学校长及研究员协会 | 四环素及其类似物的合成 |
| AU2007235279B2 (en) * | 2006-04-07 | 2012-12-06 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| KR101879751B1 (ko) | 2010-03-31 | 2018-08-16 | 테트라페이즈 파마슈티컬스, 인코포레이티드 | 폴리사이클릭 테트라사이클린 화합물 |
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Also Published As
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| KR101879751B1 (ko) | 2018-08-16 |
| DK2552890T3 (en) | 2017-04-03 |
| WO2011123536A1 (en) | 2011-10-06 |
| CN103180295B (zh) | 2016-06-08 |
| US20110269714A1 (en) | 2011-11-03 |
| US20170107179A1 (en) | 2017-04-20 |
| ES2621409T3 (es) | 2017-07-04 |
| CA2799727C (en) | 2018-06-12 |
| CN106008317A (zh) | 2016-10-12 |
| EP2552890B1 (en) | 2017-01-04 |
| AR081064A1 (es) | 2012-06-06 |
| NZ603323A (en) | 2014-12-24 |
| EP2552890A1 (en) | 2013-02-06 |
| SG184372A1 (en) | 2012-11-29 |
| CN106008317B (zh) | 2019-08-23 |
| BR112012025045A2 (pt) | 2016-06-21 |
| CA2799727A1 (en) | 2011-10-06 |
| JP2013523761A (ja) | 2013-06-17 |
| CN103180295A (zh) | 2013-06-26 |
| WO2011123536A8 (en) | 2012-02-02 |
| TW201200493A (en) | 2012-01-01 |
| AU2011235176B2 (en) | 2015-05-14 |
| TWI592390B (zh) | 2017-07-21 |
| PL2552890T3 (pl) | 2017-07-31 |
| JP5820462B2 (ja) | 2015-11-24 |
| US9371283B2 (en) | 2016-06-21 |
| JP2016014058A (ja) | 2016-01-28 |
| KR20130023231A (ko) | 2013-03-07 |
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