JP5602748B2 - トリアゾール含有マクロライドを用いた生体防御 - Google Patents
トリアゾール含有マクロライドを用いた生体防御 Download PDFInfo
- Publication number
- JP5602748B2 JP5602748B2 JP2011533399A JP2011533399A JP5602748B2 JP 5602748 B2 JP5602748 B2 JP 5602748B2 JP 2011533399 A JP2011533399 A JP 2011533399A JP 2011533399 A JP2011533399 A JP 2011533399A JP 5602748 B2 JP5602748 B2 JP 5602748B2
- Authority
- JP
- Japan
- Prior art keywords
- use according
- cem
- gonorrhea
- compound
- intracellular
- 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 - Fee Related
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 44
- 229940041033 macrolides Drugs 0.000 title description 28
- 150000003852 triazoles Chemical class 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims description 86
- 206010018612 Gonorrhoea Diseases 0.000 claims description 38
- 208000001786 gonorrhea Diseases 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 35
- -1 sulfonyl Ureido Chemical group 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 29
- 241000193738 Bacillus anthracis Species 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 18
- 229940065181 bacillus anthracis Drugs 0.000 claims description 16
- 206010035148 Plague Diseases 0.000 claims description 15
- 241000607479 Yersinia pestis Species 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000224016 Plasmodium Species 0.000 claims description 5
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 229910021386 carbon form Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 231100000569 acute exposure Toxicity 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005001 aminoaryl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002337 glycosamines Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 64
- 230000003834 intracellular effect Effects 0.000 description 59
- 210000004027 cell Anatomy 0.000 description 44
- 239000000443 aerosol Substances 0.000 description 42
- 238000012360 testing method Methods 0.000 description 35
- 239000003242 anti bacterial agent Substances 0.000 description 34
- 241001465754 Metazoa Species 0.000 description 32
- 229940088710 antibiotic agent Drugs 0.000 description 32
- 241000282693 Cercopithecidae Species 0.000 description 26
- 210000002540 macrophage Anatomy 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000003835 ketolide antibiotic agent Substances 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 21
- 230000000844 anti-bacterial effect Effects 0.000 description 21
- 229940079593 drug Drugs 0.000 description 21
- 241000894006 Bacteria Species 0.000 description 20
- 244000052769 pathogen Species 0.000 description 20
- 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
- 230000035508 accumulation Effects 0.000 description 17
- 238000009825 accumulation Methods 0.000 description 17
- 210000004369 blood Anatomy 0.000 description 17
- 239000008280 blood Substances 0.000 description 17
- 239000002054 inoculum Substances 0.000 description 17
- 230000003385 bacteriostatic effect Effects 0.000 description 16
- 230000003115 biocidal effect Effects 0.000 description 16
- 208000015181 infectious disease Diseases 0.000 description 16
- 230000004083 survival effect Effects 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 16
- 231100000111 LD50 Toxicity 0.000 description 15
- 241000191967 Staphylococcus aureus Species 0.000 description 15
- 241000193998 Streptococcus pneumoniae Species 0.000 description 13
- 230000004044 response Effects 0.000 description 13
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- 231100000673 dose–response relationship Toxicity 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 210000004072 lung Anatomy 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 230000034994 death Effects 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- 241000186779 Listeria monocytogenes Species 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 8
- 230000035567 cellular accumulation Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000007619 statistical method Methods 0.000 description 8
- 229960001722 verapamil Drugs 0.000 description 8
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 description 7
- 0 C*1(CC2)[C@]2*CC1 Chemical compound C*1(CC2)[C@]2*CC1 0.000 description 7
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 7
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 7
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 7
- 102000014842 Multidrug resistance proteins Human genes 0.000 description 7
- 108050005144 Multidrug resistance proteins Proteins 0.000 description 7
- 206010035664 Pneumonia Diseases 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 230000029142 excretion Effects 0.000 description 7
- 229960003627 gemfibrozil Drugs 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 231100000518 lethal Toxicity 0.000 description 7
- 230000001665 lethal effect Effects 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000006199 nebulizer Substances 0.000 description 7
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 241000209056 Secale Species 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 6
- 238000009534 blood test Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 241000894007 species Species 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 241000193830 Bacillus <bacterium> Species 0.000 description 5
- 108010074051 C-Reactive Protein Proteins 0.000 description 5
- 102100032752 C-reactive protein Human genes 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 241000282567 Macaca fascicularis Species 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002953 phosphate buffered saline Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 210000000952 spleen Anatomy 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- 229930191564 Monensin Natural products 0.000 description 4
- GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 description 4
- 206010057249 Phagocytosis Diseases 0.000 description 4
- 241000713311 Simian immunodeficiency virus Species 0.000 description 4
- 241000193996 Streptococcus pyogenes Species 0.000 description 4
- 238000000540 analysis of variance Methods 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 230000001332 colony forming effect Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000007154 intracellular accumulation Effects 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 229960005358 monensin Drugs 0.000 description 4
- GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- 230000008782 phagocytosis Effects 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 238000013207 serial dilution Methods 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 230000014616 translation Effects 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 241000606161 Chlamydia Species 0.000 description 3
- 206010015548 Euthanasia Diseases 0.000 description 3
- 238000000729 Fisher's exact test Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000606768 Haemophilus influenzae Species 0.000 description 3
- 241000589242 Legionella pneumophila Species 0.000 description 3
- 238000011529 RT qPCR Methods 0.000 description 3
- 241000295644 Staphylococcaceae Species 0.000 description 3
- 238000000692 Student's t-test Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 229960004099 azithromycin Drugs 0.000 description 3
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 239000000022 bacteriostatic agent Substances 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 238000009640 blood culture Methods 0.000 description 3
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000002224 dissection Methods 0.000 description 3
- 229960003276 erythromycin Drugs 0.000 description 3
- 210000003527 eukaryotic cell Anatomy 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 229940047650 haemophilus influenzae Drugs 0.000 description 3
- 210000000987 immune system Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 229940115932 legionella pneumophila Drugs 0.000 description 3
- 230000002132 lysosomal effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 230000000242 pagocytic effect Effects 0.000 description 3
- 230000003285 pharmacodynamic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012353 t test Methods 0.000 description 3
- 238000012384 transportation and delivery Methods 0.000 description 3
- 230000035899 viability Effects 0.000 description 3
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 2
- 238000007476 Maximum Likelihood Methods 0.000 description 2
- 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 2
- 241000700159 Rattus Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 101100219553 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SRV2 gene Proteins 0.000 description 2
- 241001466984 Simian T-lymphotropic virus 1 Species 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 206010000269 abscess Diseases 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 230000000941 anti-staphylcoccal effect Effects 0.000 description 2
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000000721 bacterilogical effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 238000002815 broth microdilution Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 210000000805 cytoplasm Anatomy 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000002489 hematologic effect Effects 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 231100000824 inhalation exposure Toxicity 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 238000013411 master cell bank Methods 0.000 description 2
- 229960003085 meticillin Drugs 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000001543 one-way ANOVA Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 210000003024 peritoneal macrophage Anatomy 0.000 description 2
- 210000001539 phagocyte Anatomy 0.000 description 2
- 210000000680 phagosome Anatomy 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000001243 protein synthesis Methods 0.000 description 2
- 239000000623 proton ionophore Substances 0.000 description 2
- 210000003752 saphenous vein Anatomy 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- 241001430294 unidentified retrovirus Species 0.000 description 2
- 210000003934 vacuole Anatomy 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 230000001018 virulence Effects 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- ZHTBWJDFNIADEW-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-2h-triazole Chemical group ClC1=CC=CC(Cl)=C1C1=CNN=N1 ZHTBWJDFNIADEW-UHFFFAOYSA-N 0.000 description 1
- VFRADINKOCDNSG-UHFFFAOYSA-N 5-phenyl-2h-triazol-4-amine Chemical compound N1N=NC(C=2C=CC=CC=2)=C1N VFRADINKOCDNSG-UHFFFAOYSA-N 0.000 description 1
- ZNJXVCPFQSXVQF-UHFFFAOYSA-N 6-ethynylpyridin-2-amine Chemical compound NC1=CC=CC(C#C)=N1 ZNJXVCPFQSXVQF-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- 230000035502 ADME Effects 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 208000031729 Bacteremia Diseases 0.000 description 1
- 108010077805 Bacterial Proteins Proteins 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- 206010069747 Burkholderia mallei infection Diseases 0.000 description 1
- 201000005019 Chlamydia pneumonia Diseases 0.000 description 1
- 241001647372 Chlamydia pneumoniae Species 0.000 description 1
- 241000606153 Chlamydia trachomatis Species 0.000 description 1
- 108010065152 Coagulase Proteins 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000003154 D dimer Substances 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 206010011906 Death Diseases 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 1
- 241001360526 Escherichia coli ATCC 25922 Species 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 201000003641 Glanders Diseases 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 238000003794 Gram staining Methods 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 241000092431 Listeria monocytogenes EGD Species 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 108010089503 Organic Anion Transporters Proteins 0.000 description 1
- 102000007990 Organic Anion Transporters Human genes 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 229940049937 Pgp inhibitor Drugs 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 208000035415 Reinfection Diseases 0.000 description 1
- 102000002278 Ribosomal Proteins Human genes 0.000 description 1
- 108010000605 Ribosomal Proteins Proteins 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241001312524 Streptococcus viridans Species 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 238000001793 Wilcoxon signed-rank test Methods 0.000 description 1
- PENDGIOBPJLVBT-HMMOOPTJSA-N abt-773 Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@]1(C)OC\C=C\C=1C=C2C=CC=CC2=NC=1)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O PENDGIOBPJLVBT-HMMOOPTJSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000012387 aerosolization Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 238000011203 antimicrobial therapy Methods 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 230000004700 cellular uptake Effects 0.000 description 1
- 229950010329 cethromycin Drugs 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000007330 chocolate agar Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000007820 coagulation assay Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 229960003722 doxycycline Drugs 0.000 description 1
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000556 factor analysis Methods 0.000 description 1
- 108010052295 fibrin fragment D Proteins 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 201000001371 inclusion conjunctivitis Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000002343 intraphagocytic effect Effects 0.000 description 1
- 230000006799 invasive growth in response to glucose limitation Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 238000001325 log-rank test Methods 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 210000003712 lysosome Anatomy 0.000 description 1
- 230000001868 lysosomic effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000011206 morphological examination Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- VMXAIJCDNKFKPO-UHFFFAOYSA-N n-ethynylaniline Chemical compound C#CNC1=CC=CC=C1 VMXAIJCDNKFKPO-UHFFFAOYSA-N 0.000 description 1
- KTZCMORPQBWNIP-UHFFFAOYSA-N n-ethynylpyridin-2-amine Chemical compound C#CNC1=CC=CC=N1 KTZCMORPQBWNIP-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 208000030773 pneumonia caused by chlamydia Diseases 0.000 description 1
- 230000002064 post-exposure prophylaxis Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 230000035485 pulse pressure Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000004708 ribosome subunit Anatomy 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012363 selectfluor Substances 0.000 description 1
- DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000528 statistical test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000002088 tosyl group Chemical class [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 206010044325 trachoma Diseases 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 238000007805 zymography Methods 0.000 description 1
Images
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10813408P | 2008-10-24 | 2008-10-24 | |
| US10811008P | 2008-10-24 | 2008-10-24 | |
| US10813708P | 2008-10-24 | 2008-10-24 | |
| US10816808P | 2008-10-24 | 2008-10-24 | |
| US10811208P | 2008-10-24 | 2008-10-24 | |
| US61/108,110 | 2008-10-24 | ||
| US61/108,134 | 2008-10-24 | ||
| US61/108,112 | 2008-10-24 | ||
| US61/108,137 | 2008-10-24 | ||
| US61/108,168 | 2008-10-24 | ||
| US16210909P | 2009-03-20 | 2009-03-20 | |
| US61/162,109 | 2009-03-20 | ||
| PCT/US2009/061978 WO2010048601A1 (en) | 2008-10-24 | 2009-10-24 | Biodefenses using triazole-containing macrolides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014167991A Division JP6002185B2 (ja) | 2008-10-24 | 2014-08-20 | トリアゾール含有マクロライドを用いた生体防御 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012506872A JP2012506872A (ja) | 2012-03-22 |
| JP2012506872A5 JP2012506872A5 (cg-RX-API-DMAC10.html) | 2012-12-06 |
| JP5602748B2 true JP5602748B2 (ja) | 2014-10-08 |
Family
ID=42119711
Family Applications (10)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011533399A Expired - Fee Related JP5602748B2 (ja) | 2008-10-24 | 2009-10-24 | トリアゾール含有マクロライドを用いた生体防御 |
| JP2011533397A Expired - Fee Related JP5711135B2 (ja) | 2008-10-24 | 2009-10-24 | 胃腸疾患を治療するための方法 |
| JP2011533398A Active JP5715569B2 (ja) | 2008-10-24 | 2009-10-24 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2014167991A Expired - Fee Related JP6002185B2 (ja) | 2008-10-24 | 2014-08-20 | トリアゾール含有マクロライドを用いた生体防御 |
| JP2014237428A Active JP5922210B2 (ja) | 2008-10-24 | 2014-11-25 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2014237346A Active JP5908569B2 (ja) | 2008-10-24 | 2014-11-25 | 胃腸疾患を治療するための方法 |
| JP2016080557A Active JP6309995B2 (ja) | 2008-10-24 | 2016-04-13 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2018047869A Pending JP2018115177A (ja) | 2008-10-24 | 2018-03-15 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2019189322A Pending JP2020023544A (ja) | 2008-10-24 | 2019-10-16 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2021146793A Active JP7171860B2 (ja) | 2008-10-24 | 2021-09-09 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
Family Applications After (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011533397A Expired - Fee Related JP5711135B2 (ja) | 2008-10-24 | 2009-10-24 | 胃腸疾患を治療するための方法 |
| JP2011533398A Active JP5715569B2 (ja) | 2008-10-24 | 2009-10-24 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2014167991A Expired - Fee Related JP6002185B2 (ja) | 2008-10-24 | 2014-08-20 | トリアゾール含有マクロライドを用いた生体防御 |
| JP2014237428A Active JP5922210B2 (ja) | 2008-10-24 | 2014-11-25 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2014237346A Active JP5908569B2 (ja) | 2008-10-24 | 2014-11-25 | 胃腸疾患を治療するための方法 |
| JP2016080557A Active JP6309995B2 (ja) | 2008-10-24 | 2016-04-13 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2018047869A Pending JP2018115177A (ja) | 2008-10-24 | 2018-03-15 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2019189322A Pending JP2020023544A (ja) | 2008-10-24 | 2019-10-16 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
| JP2021146793A Active JP7171860B2 (ja) | 2008-10-24 | 2021-09-09 | トリアゾール含有マクロライドを用いた耐性疾患の治療方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (7) | US9072759B2 (cg-RX-API-DMAC10.html) |
| EP (4) | EP2362727B1 (cg-RX-API-DMAC10.html) |
| JP (10) | JP5602748B2 (cg-RX-API-DMAC10.html) |
| CN (4) | CN107854477A (cg-RX-API-DMAC10.html) |
| AU (4) | AU2009308181B2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK2358379T3 (cg-RX-API-DMAC10.html) |
| ES (3) | ES2676168T3 (cg-RX-API-DMAC10.html) |
| HK (1) | HK1252140A1 (cg-RX-API-DMAC10.html) |
| HR (1) | HRP20160222T1 (cg-RX-API-DMAC10.html) |
| SI (1) | SI2358379T1 (cg-RX-API-DMAC10.html) |
| WO (3) | WO2010048601A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3738591A3 (en) | 2003-03-10 | 2021-03-24 | Merck Sharp & Dohme Corp. | Novel antibacterial agents |
| WO2009055557A1 (en) | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| DK2358379T3 (en) | 2008-10-24 | 2016-03-07 | Cempra Pharmaceuticals Inc | BIOFORSVAR USING TRIAZOLHOLDIGE macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| EP2475253B1 (en) | 2009-09-10 | 2016-10-26 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and mac diseases |
| JP5711352B2 (ja) * | 2010-03-22 | 2015-04-30 | センプラ ファーマシューティカルズ，インコーポレイテッド | マクロライドの結晶形、およびその使用 |
| WO2011146829A1 (en) * | 2010-05-20 | 2011-11-24 | Cempra Pharmaceuticals, Inc. | Processes for preparing macrolides and ketolides and intermediates therefor |
| US9815863B2 (en) | 2010-09-10 | 2017-11-14 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| US10188674B2 (en) | 2012-03-27 | 2019-01-29 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| EP2968801B1 (en) * | 2013-03-14 | 2018-09-26 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| CN105188712A (zh) | 2013-03-15 | 2015-12-23 | 森普拉制药公司 | 用于制备大环内酯抗菌剂的收敛方法 |
| CA3130061C (en) | 2013-04-04 | 2024-05-28 | President And Fellows Of Harvard College | Macrolides and methods of their preparation and use |
| CN104151382B (zh) * | 2014-08-08 | 2016-09-14 | 广东东阳光药业有限公司 | 一种固态大环内酯的晶型 |
| CN104311611B (zh) * | 2014-08-13 | 2017-01-18 | 广东东阳光药业有限公司 | 一种制备固态大环内酯的方法 |
| WO2016057798A1 (en) | 2014-10-08 | 2016-04-14 | President And Fellows Of Harvard College | 14-membered ketolides and methods of their preparation and use |
| EP3273969A4 (en) * | 2015-03-25 | 2018-11-21 | President and Fellows of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| CN106554992A (zh) * | 2015-09-28 | 2017-04-05 | 中国疾病预防控制中心传染病预防控制所 | 检测耐红霉素弯曲菌的试剂盒 |
| WO2018152424A1 (en) * | 2017-02-17 | 2018-08-23 | Cempra Pharmaceuticals, Inc. | Triazole-containing macrolides and ophthalmic uses therefor |
| US10706191B2 (en) * | 2017-08-31 | 2020-07-07 | Google Llc | Systems and methods for generating a geo-level hierarchical Bayesian model |
| US11145299B2 (en) | 2018-04-19 | 2021-10-12 | X Development Llc | Managing voice interface devices |
Family Cites Families (129)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1354753A (en) | 1919-02-11 | 1920-10-05 | E M Lannes | Portable building |
| US2180006A (en) | 1936-09-09 | 1939-11-14 | Eastman Kodak Co | Process for the separation and refining of amines |
| GB891817A (en) | 1959-04-07 | 1962-03-21 | Upjohn Co | Improvements in or relating to injectable tetracyclic preparations |
| US3843787A (en) | 1969-01-15 | 1974-10-22 | Pierrel Spa | Water soluble derivative of erythromycin |
| US3668282A (en) | 1970-05-08 | 1972-06-06 | Stauffer Chemical Co | Stabilized mixture employing n-(beta-0,0-dialkyldithiophosphoryl) aryl sulfonamides |
| SE458505B (sv) | 1979-07-10 | 1989-04-10 | Lepetit Spa | Anvaendningen av rifamycin sv och salter daerav foer framstaellning av en beredning foer behandling av reumatoid artrit samt vissa av salterna och deras framstaellning |
| US4331803A (en) * | 1980-06-04 | 1982-05-25 | Taisho Pharmaceutical Co., Ltd. | Novel erythromycin compounds |
| US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| JPS59175414A (ja) | 1983-03-23 | 1984-10-04 | Toyo Jozo Co Ltd | マクロライド抗生物質の安定な経口用製剤および安定化法 |
| US4742049A (en) * | 1986-06-04 | 1988-05-03 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| KR960000434B1 (ko) | 1986-12-17 | 1996-01-06 | 다이쇼 세이야꾸 가부시끼가이샤 | 에리스로마이신 a유도체 및 그의 제조 방법 |
| HU198913B (en) | 1987-09-03 | 1989-12-28 | Pliva Pharm & Chem Works | Process for producing 10-dihydro-10-deoxo-11-aza-erythronolide a-derivatives and pharmaceutical compositions containing them as active components |
| BE1001869A3 (fr) | 1988-10-12 | 1990-04-03 | Franz Legros | Procede d'encapsulation liposomiale d'antibiotiques aminoglucosidiques, en particulier de la gentamycine. |
| IL114589A (en) * | 1990-11-21 | 1999-12-22 | Roussel Uclaf | Intermediates for the preparation of erythromycin derivatives |
| US5985844A (en) * | 1992-03-26 | 1999-11-16 | Merck & Co., Inc. | Homoerythromycin A derivatives modified at the 4"-and 8A-positions |
| US5527780A (en) | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2719587B1 (fr) | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5834428A (en) * | 1995-04-14 | 1998-11-10 | 1149336 Ontario Inc. | Glucagon-like peptide-2 and its therapeutic use |
| WO1997001532A1 (en) * | 1995-06-28 | 1997-01-16 | Tokuyama Corporation | Ketonitrile derivatives and antibacterial agent and drug containing the same |
| FR2739620B1 (fr) * | 1995-10-09 | 1997-12-19 | Roussel Uclaf | Nouveaux derives de la 5-0-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
| US6274715B1 (en) | 1995-11-08 | 2001-08-14 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| US5742049A (en) * | 1995-12-21 | 1998-04-21 | Bruker-Franzen Analytik Gmbh | Method of improving mass resolution in time-of-flight mass spectrometry |
| FR2742757B1 (fr) | 1995-12-22 | 1998-01-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2745290B1 (fr) * | 1996-02-28 | 1998-04-03 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US5719272A (en) | 1996-04-02 | 1998-02-17 | Abbott Laboratories | 2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives |
| KR100576988B1 (ko) * | 1996-09-04 | 2006-05-10 | 아보트 러보러터리즈 | 항균 활성을 지닌 6-ｏ-치환된 케톨라이드 |
| KR20000069431A (ko) | 1996-12-13 | 2000-11-25 | 피터 지. 스트링거 | Ｐｓａ의 효소 활성 억제제 |
| HN1998000086A (es) | 1997-06-11 | 1999-03-08 | Pfizer Prod Inc | Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos. |
| US6407074B1 (en) * | 1997-06-11 | 2002-06-18 | Pfizer Inc | C-4″-substituted macrolide derivatives |
| HN1998000074A (es) | 1997-06-11 | 1999-01-08 | Pfizer Prod Inc | Derivados de macrolidos c-4 sustituidos |
| KR20010013660A (ko) | 1997-06-11 | 2001-02-26 | 실버스타인 아써 에이. | 9-옥심 에리트로마이신 유도체 |
| HN1998000159A (es) | 1997-10-29 | 1999-02-09 | Monsanto Co | Derivados de 9- amino - 3 ceto eritromicina |
| IL135792A0 (en) | 1997-12-01 | 2001-05-20 | Abbott Lab | 6-o-alkyl derivatives of erythronolide b |
| ID27825A (id) * | 1998-03-26 | 2001-04-26 | Fujisawa Pharmaceutical Co | Sediaan lepas lambat |
| FR2777282B1 (fr) * | 1998-04-08 | 2001-04-20 | Hoechst Marion Roussel Inc | Nouveaux derives de la 2-fluoro 3-de((2,6-dideoxy 3-c-methyl 3-0-methyl-alpha-l-ribohexopyranosyl) oxyl) 6-o-methyl 3-oxo erythromycine, leur procede de preparation et leur application a la synthese de principes actifs de medicaments |
| US6020521A (en) * | 1998-08-26 | 2000-02-01 | Abbott Laboratories | Macrolide LHRH antagonists |
| US6387885B1 (en) | 1998-08-26 | 2002-05-14 | Abbott Laboratories | 3′,3′-N-bis-desmethyl-3′-N-cycloalkyl erythromycin derivatives as LHRH antagonists |
| FR2785612A1 (fr) * | 1998-11-10 | 2000-05-12 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2786188B1 (fr) | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
| KR100317907B1 (ko) | 1998-11-24 | 2001-12-24 | 김 완 주 | 신규한 중간체, 이를 이용한 마크로라이드계 항생제의제조방법 |
| DE69933897T2 (de) | 1998-12-10 | 2007-03-15 | Pfizer Products Inc., Groton | Carbamat- und Carbazatketolid-Antibiotika |
| ATE256694T1 (de) | 1999-01-27 | 2004-01-15 | Pfizer Prod Inc | Ketolid-antibiotika |
| CA2292359C (en) | 1999-01-28 | 2004-09-28 | Pfizer Products Inc. | Novel azalides and methods of making same |
| FR2789392B1 (fr) | 1999-02-04 | 2001-10-05 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| JP2000351794A (ja) | 1999-04-08 | 2000-12-19 | Hokuriku Seiyaku Co Ltd | エリスロマイシン誘導体 |
| AR023264A1 (es) | 1999-04-08 | 2002-09-04 | Hokuriku Pharmaceutical | Derivados de eritromicina |
| EP1171447A2 (en) | 1999-04-16 | 2002-01-16 | Ortho-McNeil Pharmaceutical, Inc. | Ketolide antibacterials |
| NZ515027A (en) * | 1999-04-16 | 2004-01-30 | Kosan Biosciences Inc | Erythromycin derivatives as antibiotics |
| US6395300B1 (en) | 1999-05-27 | 2002-05-28 | Acusphere, Inc. | Porous drug matrices and methods of manufacture thereof |
| US6420535B1 (en) | 1999-06-07 | 2002-07-16 | Abbott Laboratories | 6-O-carbamate ketolide derivatives |
| US6437106B1 (en) | 1999-06-24 | 2002-08-20 | Abbott Laboratories | Process for preparing 6-o-substituted erythromycin derivatives |
| AU6183700A (en) | 1999-08-06 | 2001-03-05 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| AU3337900A (en) | 1999-08-09 | 2001-03-05 | Eric Au | An apparatus for treating wastewater |
| US6096922A (en) | 1999-11-01 | 2000-08-01 | Air Products And Chemicals, Inc. | Process for the synthesis of dialkyl, diaryl, and arylalkyl aminosulfur trifluorides |
| KR100336447B1 (ko) | 1999-11-24 | 2002-05-15 | 민경윤 | 클라리스로마이신의 개선된 제조방법 |
| JP2001261694A (ja) * | 2000-03-06 | 2001-09-26 | Pfizer Prod Inc | ケトライド抗生物質 |
| ES2242668T3 (es) * | 2000-03-15 | 2005-11-16 | Hanmi Pharm. Co., Ltd. | Metodo para obtener claritromicina en cristales de forma ii. |
| NZ523693A (en) | 2000-07-10 | 2004-08-27 | Chiron Corp | Macrolide formulations for inhalation and methods of treatment of endobronchial infections |
| US20020115621A1 (en) * | 2000-08-07 | 2002-08-22 | Wei-Gu Su | Macrolide antibiotics |
| GB0031312D0 (en) | 2000-12-21 | 2001-02-07 | Glaxo Group Ltd | Macrolides |
| EP1320355B1 (en) * | 2001-05-18 | 2006-04-05 | Chiron Corporation | System for delivering a tobramycin formulation |
| AU2002316550A1 (en) | 2001-07-03 | 2003-01-21 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| US20030176327A1 (en) * | 2001-10-25 | 2003-09-18 | Cassell Gail Houston | Antibiotics for treating biohazardous bacterial agents |
| US20040019012A1 (en) | 2002-02-22 | 2004-01-29 | Singh Satish K. | Ophthalmic antibiotic drug formulations containing a cyclodextrin compound and cetyl pyridinium chloride |
| KR101048279B1 (ko) * | 2002-05-30 | 2011-07-13 | 더 스크립스 리서치 인스티튜트 | 구리 촉매 작용하에서의 아지드와 아세틸렌과의 리게이션 |
| CA2491846A1 (en) * | 2002-06-17 | 2003-12-24 | Epigenesis Pharmaceuticals Llc | Dihydrate dehydroepiandrosterone and methods of treating asthma or chronic obstructive pulmonary disease using compositions thereof |
| AU2003255851B2 (en) | 2002-07-08 | 2009-07-23 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | New compounds, compositions and methods for treatment of inflammatory diseases and conditions |
| US7091196B2 (en) * | 2002-09-26 | 2006-08-15 | Rib-X Pharmaceuticals, Inc. | Bifunctional heterocyclic compounds and methods of making and using same |
| ITMI20022292A1 (it) * | 2002-10-29 | 2004-04-30 | Zambon Spa | 9a-azalidi ad attivita' antiinfiammatoria. |
| EP3738591A3 (en) | 2003-03-10 | 2021-03-24 | Merck Sharp & Dohme Corp. | Novel antibacterial agents |
| WO2004096823A2 (en) | 2003-04-25 | 2004-11-11 | Chiron Corporation | Novel ketolide derivatives |
| WO2004096822A2 (en) | 2003-04-25 | 2004-11-11 | Chiron Corporation | Pyridyl substituted ketolide antibiotics |
| PT1628989E (pt) | 2003-05-13 | 2007-03-30 | Glaxo Group Ltd | Novos compostos anelares com 14 e 15 membros |
| US20050014706A1 (en) | 2003-07-14 | 2005-01-20 | Kanakeshwari Falzari | Method of treating tuberculosis |
| US7457520B2 (en) * | 2003-07-24 | 2008-11-25 | Time Warner Cable, Inc. | Technique for providing a virtual digital video recorder service through a communications network |
| GB0402578D0 (en) | 2004-02-05 | 2004-03-10 | Cambridge Theranostics Ltd | Methods of treatment of atherosclerosis |
| US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| CA2559281A1 (en) | 2004-04-28 | 2005-11-10 | Alembic Limited | Process for the preparation of telithromycin |
| AU2005240849B2 (en) | 2004-05-06 | 2008-10-23 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Ester linked macrolides useful for the treatment of microbial infections |
| WO2006080954A1 (en) * | 2004-07-28 | 2006-08-03 | Ranbaxy Laboratories Limited | Ketolide derivatives as antibacterial agents |
| GB0424958D0 (en) | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424959D0 (en) | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| JP2008526947A (ja) | 2005-01-14 | 2008-07-24 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | 抗マラリア活性を有する９ａ−カルバモイル−γ−アミノプロピル−および９ａ−チオカルバモイル−γ−アミノプロピル−アザリド |
| US20080227730A1 (en) | 2005-01-14 | 2008-09-18 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | 9A-Carbamoyl and Thiocarbamoyl Azalides With Antimalarial Activity |
| ATE523519T1 (de) | 2005-01-14 | 2011-09-15 | Glaxo Group Ltd | Makrolidverbindungen mit biotin und fotoaffinitätsgruppe zur identifizierung eines makrolid-targets |
| CA2601709C (en) | 2005-03-22 | 2017-02-14 | Azevan Pharmaceuticals, Inc. | Beta-lactamylalkanoic acids |
| CA2614412A1 (en) | 2005-07-07 | 2007-01-18 | Elan Pharma International, Limited | Nanoparticulate clarithromycin formulations |
| EP1910346B1 (en) | 2005-07-19 | 2019-02-27 | Azevan Pharmaceuticals, Inc. | Beta-lactamyl phenylalanine, cysteine, and serine vasopressin antagonist |
| JP5405114B2 (ja) | 2005-10-31 | 2014-02-05 | レオ ファーマ アクティーゼルスカブ | 抗生物質である結晶フシジン酸の調製 |
| GB0522715D0 (en) | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
| US20070167382A1 (en) * | 2005-11-15 | 2007-07-19 | Nina Finkelstein | Crystalline and amorphous forms of telithromycin |
| US20090005325A1 (en) * | 2005-11-23 | 2009-01-01 | Biswajit Bas | Ketolide Derivatives as Antibacterial Agents |
| US20090075916A1 (en) * | 2005-11-23 | 2009-03-19 | Upadhyay Dilip J | Use of Macrolide Derivatives for Treating Acne |
| DOP2006000268A (es) * | 2005-12-22 | 2007-07-31 | Pfizer Prod Inc | Agentes antibacterianos |
| CN101045063B (zh) | 2006-03-28 | 2011-01-26 | 广州朗圣药业有限公司 | 注射用克拉霉素水溶性制剂 |
| JP5126685B2 (ja) | 2006-05-01 | 2013-01-23 | 大正製薬株式会社 | マクロライド誘導体 |
| WO2007143507A2 (en) | 2006-06-05 | 2007-12-13 | Auspex Pharmaceuticals, Inc. | Preparation and utility of substituted erythromycin analogs |
| DE102006036199B4 (de) * | 2006-08-03 | 2016-01-07 | Deere & Company | Förderzusammenbau und Presse |
| CN101129383B (zh) * | 2006-08-25 | 2014-04-02 | 天津和美生物技术有限公司 | 含氨基糖苷类抗生素的抗生素复方 |
| WO2009055557A1 (en) * | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| US20090209547A1 (en) * | 2008-02-15 | 2009-08-20 | In Jong Kim | C-8 halogenated macrolides |
| DK2358379T3 (en) * | 2008-10-24 | 2016-03-07 | Cempra Pharmaceuticals Inc | BIOFORSVAR USING TRIAZOLHOLDIGE macrolides |
| US9814657B2 (en) | 2009-04-27 | 2017-11-14 | Premier Dental Products Company | Buffered microencapsulated compositions and methods |
| WO2011008193A1 (en) | 2009-07-13 | 2011-01-20 | Cempra Pharmaceuticals Inc. | Fusidic acid dosing regimens for treatment of bacterial infections |
| EP2475253B1 (en) | 2009-09-10 | 2016-10-26 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and mac diseases |
| US20110119604A1 (en) | 2009-11-19 | 2011-05-19 | Clevest Solutions Inc. | System and method for a configurable and extensible allocation and scheduling tool |
| CN109091489A (zh) | 2010-03-10 | 2018-12-28 | 森普拉制药公司 | 大环内酯类抗生素的肠胃外制剂 |
| JP5711352B2 (ja) | 2010-03-22 | 2015-04-30 | センプラ ファーマシューティカルズ，インコーポレイテッド | マクロライドの結晶形、およびその使用 |
| WO2011146829A1 (en) | 2010-05-20 | 2011-11-24 | Cempra Pharmaceuticals, Inc. | Processes for preparing macrolides and ketolides and intermediates therefor |
| US8247394B2 (en) | 2010-06-02 | 2012-08-21 | Cempra Pharmaceuticals Inc. | Methods of treating urethritis and related infections using fusidic acid |
| US9260473B2 (en) | 2010-07-19 | 2016-02-16 | Virginia Commonwealth University | Bivalent multifunctional ligands targeting Aβ oligomers as treatment for Alzheimer's disease |
| WO2012030513A2 (en) | 2010-08-30 | 2012-03-08 | Cempra Pharmaceuticals Inc. | Methods of treating bacterial infections through pulmonary delivery of fusidic acid |
| US9815863B2 (en) | 2010-09-10 | 2017-11-14 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| WO2012042534A2 (en) | 2010-09-28 | 2012-04-05 | Glenmark Generics Limited | Processes for the preparation of r-sitagliptin and intermediates thereof |
| WO2012162439A2 (en) | 2011-05-23 | 2012-11-29 | Cem-102 Pharmaceuticals, Inc. | Compositions comprising fusidic acid and packages therefor |
| EP2748165B1 (en) | 2011-08-27 | 2016-11-02 | Wockhardt Limited | 1,6-diazabicyclo[3,2,1]octan-7-one derivatives and their use in the treatment of bacterial infections. |
| HK1199725A1 (en) | 2011-08-29 | 2015-07-17 | 无限药品股份有限公司 | Heterocyclic compounds and uses thereof |
| WO2013059610A1 (en) | 2011-10-20 | 2013-04-25 | Trius Therapeutics, Inc. | Therapeutic combination of daptomycin and protein synthesis inhibitor antibiotic, and methods of use |
| US10188674B2 (en) | 2012-03-27 | 2019-01-29 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| EP2968801B1 (en) | 2013-03-14 | 2018-09-26 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| CN105188712A (zh) | 2013-03-15 | 2015-12-23 | 森普拉制药公司 | 用于制备大环内酯抗菌剂的收敛方法 |
| CA3130061C (en) | 2013-04-04 | 2024-05-28 | President And Fellows Of Harvard College | Macrolides and methods of their preparation and use |
| WO2015123256A1 (en) | 2014-02-14 | 2015-08-20 | Cempra Pharmaceuticals, Inc. | Compositions and methods for treating diabetes and liver diseases |
| EP3148966A1 (en) | 2014-05-27 | 2017-04-05 | Dipharma Francis S.r.l. | Azidoalkylamine salts and their use as intermediates |
| CA2957034A1 (en) | 2014-08-05 | 2016-02-11 | Cempra Pharmaceuticals, Inc. | Powder oral suspension formulations of antibacterial agents |
| CN107405355A (zh) | 2015-03-06 | 2017-11-28 | 森普拉制药公司 | 用于制备氟酮内酯的方法 |
-
2009
- 2009-10-24 DK DK09822828.1T patent/DK2358379T3/en active
- 2009-10-24 WO PCT/US2009/061978 patent/WO2010048601A1/en not_active Ceased
- 2009-10-24 SI SI200931385A patent/SI2358379T1/sl unknown
- 2009-10-24 EP EP09822827.3A patent/EP2362727B1/en not_active Not-in-force
- 2009-10-24 US US13/125,550 patent/US9072759B2/en not_active Expired - Fee Related
- 2009-10-24 EP EP09822826.5A patent/EP2365747B1/en not_active Not-in-force
- 2009-10-24 US US13/125,551 patent/US8791080B2/en not_active Expired - Fee Related
- 2009-10-24 ES ES09822826.5T patent/ES2676168T3/es active Active
- 2009-10-24 CN CN201711145739.1A patent/CN107854477A/zh active Pending
- 2009-10-24 HR HRP20160222TT patent/HRP20160222T1/hr unknown
- 2009-10-24 CN CN200980150068.5A patent/CN102245195B/zh not_active Expired - Fee Related
- 2009-10-24 AU AU2009308181A patent/AU2009308181B2/en not_active Ceased
- 2009-10-24 AU AU2009308180A patent/AU2009308180B2/en not_active Ceased
- 2009-10-24 US US13/125,555 patent/US8796232B2/en not_active Expired - Fee Related
- 2009-10-24 EP EP15186676.1A patent/EP3031460A1/en not_active Withdrawn
- 2009-10-24 JP JP2011533399A patent/JP5602748B2/ja not_active Expired - Fee Related
- 2009-10-24 JP JP2011533397A patent/JP5711135B2/ja not_active Expired - Fee Related
- 2009-10-24 AU AU2009308182A patent/AU2009308182B2/en not_active Ceased
- 2009-10-24 CN CN201610045028.6A patent/CN105616437A/zh active Pending
- 2009-10-24 WO PCT/US2009/061977 patent/WO2010048600A1/en not_active Ceased
- 2009-10-24 CN CN200980146721.0A patent/CN102223794B/zh not_active Expired - Fee Related
- 2009-10-24 ES ES09822827.3T patent/ES2677007T3/es active Active
- 2009-10-24 WO PCT/US2009/061976 patent/WO2010048599A1/en not_active Ceased
- 2009-10-24 EP EP09822828.1A patent/EP2358379B1/en not_active Not-in-force
- 2009-10-24 ES ES09822828.1T patent/ES2565083T3/es active Active
- 2009-10-24 JP JP2011533398A patent/JP5715569B2/ja active Active
-
2014
- 2014-06-19 US US14/309,178 patent/US9439918B2/en not_active Expired - Fee Related
- 2014-06-19 US US14/309,202 patent/US9901592B2/en not_active Expired - Fee Related
- 2014-08-20 JP JP2014167991A patent/JP6002185B2/ja not_active Expired - Fee Related
- 2014-11-25 JP JP2014237428A patent/JP5922210B2/ja active Active
- 2014-11-25 JP JP2014237346A patent/JP5908569B2/ja active Active
-
2015
- 2015-05-29 US US14/725,247 patent/US9669046B2/en not_active Expired - Fee Related
-
2016
- 2016-04-13 JP JP2016080557A patent/JP6309995B2/ja active Active
- 2016-04-28 AU AU2016202707A patent/AU2016202707A1/en not_active Abandoned
-
2018
- 2018-01-19 US US15/875,187 patent/US20180369262A1/en not_active Abandoned
- 2018-03-15 JP JP2018047869A patent/JP2018115177A/ja active Pending
- 2018-09-07 HK HK18111531.3A patent/HK1252140A1/zh unknown
-
2019
- 2019-10-16 JP JP2019189322A patent/JP2020023544A/ja active Pending
-
2021
- 2021-09-09 JP JP2021146793A patent/JP7171860B2/ja active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6002185B2 (ja) | トリアゾール含有マクロライドを用いた生体防御 | |
| JP7322259B2 (ja) | 真菌感染の処置のための投薬レジメン | |
| Nosanchuk | Current status and future of antifungal therapy for systemic mycoses | |
| WO2013013178A1 (en) | Sesquiterpenes for antifungal applications | |
| HK1224922A (en) | Biodefenses using triazole-containing macrolides | |
| HK1224922A1 (en) | Biodefenses using triazole-containing macrolides | |
| HK1224595A1 (en) | Biodefenses using triazole-containing macrolides | |
| HK1224595A (en) | Biodefenses using triazole-containing macrolides | |
| EP3769622A1 (en) | Antimycotic | |
| TW202110441A (zh) | 用於消除耳念珠菌移生之抗真菌劑 | |
| Dalhoff | Interaction of Quinolones with Host—Parasite Relationship | |
| HK40067174A (zh) | 用於消除耳念珠菌移生的如依贝瑞芬赫普的抗真菌剂 | |
| HK1261465A1 (en) | Dosing regimens for treatment of fungal infections |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121016 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20121016 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131224 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140320 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140328 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140422 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140430 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140523 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140530 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140624 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140722 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140820 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5602748 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |