KR20180110181A - 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 - Google Patents
질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 Download PDFInfo
- Publication number
- KR20180110181A KR20180110181A KR1020187027659A KR20187027659A KR20180110181A KR 20180110181 A KR20180110181 A KR 20180110181A KR 1020187027659 A KR1020187027659 A KR 1020187027659A KR 20187027659 A KR20187027659 A KR 20187027659A KR 20180110181 A KR20180110181 A KR 20180110181A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- cem
- ribosomes
- 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.)
- Ceased
Links
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 57
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 16
- 239000001257 hydrogen Substances 0.000 title description 53
- 125000001153 fluoro group Chemical group F* 0.000 title description 18
- 239000003835 ketolide antibiotic agent Substances 0.000 title description 15
- 201000010099 disease Diseases 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 79
- 150000001875 compounds Chemical class 0.000 claims description 140
- -1 benzimidazolinyl Chemical group 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 28
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 claims description 25
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 claims description 25
- 208000035143 Bacterial infection Diseases 0.000 claims description 20
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000000069 prophylactic effect Effects 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000026423 prostatic infection Diseases 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract description 38
- 150000004677 hydrates Chemical class 0.000 abstract description 23
- 239000012453 solvate Substances 0.000 abstract description 23
- 230000001580 bacterial effect Effects 0.000 abstract description 20
- 239000003242 anti bacterial agent Substances 0.000 abstract description 17
- 239000004599 antimicrobial Substances 0.000 abstract description 4
- 210000003705 ribosome Anatomy 0.000 description 76
- IXXFZUPTQVDPPK-ZAWHAJPISA-N (1r,2r,4r,6r,7r,8r,10s,13r,14s)-17-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-7-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-10-fluoro-6-methoxy-2,4,6,8,10,14-hexamethyl-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tet Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@](C)(F)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3N=NC(=C3)C=3C=C(N)C=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IXXFZUPTQVDPPK-ZAWHAJPISA-N 0.000 description 68
- 230000003993 interaction Effects 0.000 description 61
- 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 56
- 241000588724 Escherichia coli Species 0.000 description 43
- 229960003250 telithromycin Drugs 0.000 description 43
- LJVAJPDWBABPEJ-PNUFFHFMSA-N telithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3C=C(N=C3)C=3C=NC=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O LJVAJPDWBABPEJ-PNUFFHFMSA-N 0.000 description 42
- 230000027455 binding Effects 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 206010057190 Respiratory tract infections Diseases 0.000 description 32
- 229960003276 erythromycin Drugs 0.000 description 29
- 229940079593 drug Drugs 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000004429 atom Chemical group 0.000 description 20
- 241000191967 Staphylococcus aureus Species 0.000 description 19
- 239000002243 precursor Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 230000014616 translation Effects 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 238000013519 translation Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 229960002626 clarithromycin Drugs 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 13
- 241000894006 Bacteria Species 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000007931 macrolactones Chemical group 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 229940088710 antibiotic agent Drugs 0.000 description 12
- 229940041033 macrolides Drugs 0.000 description 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000004048 modification Effects 0.000 description 11
- 238000012986 modification Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 238000002474 experimental method Methods 0.000 description 10
- 150000002337 glycosamines Chemical group 0.000 description 10
- 150000002596 lactones Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000004224 protection Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 244000052616 bacterial pathogen Species 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 230000003115 biocidal effect Effects 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 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 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960004099 azithromycin Drugs 0.000 description 6
- 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 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000001243 protein synthesis Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- YRCRRHNVYVFNTM-UHFFFAOYSA-N 1,1-dihydroxy-3-ethoxy-2-butanone Chemical compound CCOC(C)C(=O)C(O)O YRCRRHNVYVFNTM-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 241000193998 Streptococcus pneumoniae Species 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229950001103 ketoxal Drugs 0.000 description 5
- 210000001069 large ribosome subunit Anatomy 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 230000011987 methylation Effects 0.000 description 5
- 238000007069 methylation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 108010077805 Bacterial Proteins Proteins 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 108060004795 Methyltransferase Proteins 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 4
- KYTWXIARANQMCA-RWJQBGPGSA-N (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2 Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=NO)[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 KYTWXIARANQMCA-RWJQBGPGSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 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
- 108020004414 DNA Proteins 0.000 description 3
- 108060001084 Luciferase Proteins 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- 102000016397 Methyltransferase Human genes 0.000 description 3
- 108090000279 Peptidyltransferases Proteins 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000009137 competitive binding Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000012866 crystallographic experiment Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 108020004999 messenger RNA Proteins 0.000 description 3
- 238000003032 molecular docking Methods 0.000 description 3
- 125000006308 propyl amino group Chemical group 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 108020005097 23S Ribosomal RNA Proteins 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000192091 Deinococcus radiodurans Species 0.000 description 2
- 206010013710 Drug interaction Diseases 0.000 description 2
- 101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 2
- 229930006677 Erythromycin A Natural products 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 2
- 241000205065 Haloarcula Species 0.000 description 2
- 241000205063 Haloarcula marismortui Species 0.000 description 2
- 102100034343 Integrase Human genes 0.000 description 2
- 241000270322 Lepidosauria Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005094 computer simulation Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 101150076810 erm gene Proteins 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 244000000059 gram-positive pathogen Species 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 101150111763 mefA gene Proteins 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 2
- 150000007523 nucleic acids Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000006916 protein interaction Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 210000001995 reticulocyte Anatomy 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000005966 1,2,4-thiadiazolidinyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000005965 1,3,4-oxadiazolidinyl group Chemical group 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000005967 1,3,4-thiadiazolidinyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical class OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 1
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical group C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- BFSUQRCCKXZXEX-UHFFFAOYSA-N 2-methoxypropan-2-ol Chemical compound COC(C)(C)O BFSUQRCCKXZXEX-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 241000203069 Archaea Species 0.000 description 1
- 229930188120 Carbomycin Natural products 0.000 description 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 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 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101710141795 Ribonuclease inhibitor Proteins 0.000 description 1
- 229940122208 Ribonuclease inhibitor Drugs 0.000 description 1
- 102100037968 Ribonuclease inhibitor Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 201000005010 Streptococcus pneumonia Diseases 0.000 description 1
- 108010066860 Vernamycin B Proteins 0.000 description 1
- FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 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
- 238000009825 accumulation Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000012984 antibiotic solution Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229950005779 carbomycin Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229950010329 cethromycin Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012875 competitive assay Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 150000008266 deoxy sugars Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000012869 ethanol precipitation Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 1
- 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 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 238000012009 microbiological test Methods 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 150000003881 polyketide derivatives Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- GUUBJKMBDULZTE-UHFFFAOYSA-M potassium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[K+].OCCN1CCN(CCS(O)(=O)=O)CC1 GUUBJKMBDULZTE-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 108010042660 rRNA (adenosine-O-2'-)methyltransferase Proteins 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005756 tetralinylene group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000036964 tight binding Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 238000012070 whole genome sequencing analysis Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
-
- 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
- A61P33/04—Amoebicides
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38179410P | 2010-09-10 | 2010-09-10 | |
| US61/381,794 | 2010-09-10 | ||
| PCT/US2011/051064 WO2012034058A1 (en) | 2010-09-10 | 2011-09-09 | Hydrogen bond forming fluoro ketolides for treating diseases |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137009177A Division KR20130120458A (ko) | 2010-09-10 | 2011-09-09 | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180110181A true KR20180110181A (ko) | 2018-10-08 |
Family
ID=45810985
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187027659A Ceased KR20180110181A (ko) | 2010-09-10 | 2011-09-09 | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| KR1020137009177A Ceased KR20130120458A (ko) | 2010-09-10 | 2011-09-09 | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137009177A Ceased KR20130120458A (ko) | 2010-09-10 | 2011-09-09 | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9815863B2 (enExample) |
| EP (1) | EP2613630A4 (enExample) |
| JP (1) | JP6042334B2 (enExample) |
| KR (2) | KR20180110181A (enExample) |
| WO (1) | WO2012034058A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1638549A4 (en) | 2003-03-10 | 2011-06-15 | Optimer Pharmaceuticals Inc | NEW ANTIBACTERIAL AGENTS |
| US9453042B2 (en) | 2007-10-25 | 2016-09-27 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| HRP20160222T1 (hr) | 2008-10-24 | 2016-04-08 | Cempra Pharmaceuticals, Inc. | Biozaštite uporabom makrolida koji sadrže triazol |
| 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 |
| CN102917708B (zh) | 2010-05-20 | 2015-11-25 | 森普拉制药公司 | 制备大环内酯和酮内酯及其中间体的方法 |
| US9815863B2 (en) | 2010-09-10 | 2017-11-14 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| IN2014DN08939A (enExample) | 2012-03-27 | 2015-05-22 | Cempra Pharmaceuticals Inc | |
| CN103897002A (zh) * | 2012-12-31 | 2014-07-02 | 菏泽市方明制药有限公司 | 一种粗品硫氰酸红霉素制备红霉素a9-肟的方法 |
| CA2905975A1 (en) | 2013-03-14 | 2014-09-25 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| EP2968384A4 (en) | 2013-03-15 | 2017-02-15 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| MX377459B (es) | 2013-04-04 | 2025-03-10 | Harvard College | Macrolidos y metodos para su preparacion y uso. |
| WO2016057798A1 (en) * | 2014-10-08 | 2016-04-14 | President And Fellows Of Harvard College | 14-membered ketolides and methods of their preparation and use |
| WO2016154591A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
Family Cites Families (120)
| 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 |
| 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 |
| EP0283055B1 (en) | 1987-09-03 | 1990-08-29 | SOUR PLIVA farmaceutska, Kemijska prehrambena i kozmeticka industrija, n.sol.o. | 10-dihydro-10-deoxo-11-azaerythronolide-a-compounds, methods and intermediates for the manufacture thereof and their use in pharmaceuticals and in the manufacture thereof |
| 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. |
| FR2732684B1 (fr) * | 1995-04-06 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US5834428A (en) | 1995-04-14 | 1998-11-10 | 1149336 Ontario Inc. | Glucagon-like peptide-2 and its therapeutic use |
| 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 |
| 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 |
| ATE296308T1 (de) | 1996-09-04 | 2005-06-15 | Abbott Lab | 6-o-substituierte ketoliden mit antibakteriellen wirkung |
| HUP0000288A3 (en) | 1996-12-13 | 2001-04-28 | Lilly Co Eli | Azetidinone derivatives as inhibitors of the enzymatic activity of psa, intermediates, process for their preparation and pharmaceutical compositions thereof |
| 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 |
| ID24529A (id) | 1997-06-11 | 2000-07-20 | Pfizer Prod Inc | Turunan-turunan 9-oksima eritromisin |
| HN1998000159A (es) | 1997-10-29 | 1999-02-09 | Monsanto Co | Derivados de 9- amino - 3 ceto eritromicina |
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| FR2771008B1 (fr) * | 1997-11-17 | 2000-04-28 | Hoechst Marion Roussel Inc | Utilisation des ketolides pour la preparation de compositions pharmaceutiques destinees a prevenir les complications thrombotiques arterielles liees a l'atherosclerose |
| IL135792A0 (en) | 1997-12-01 | 2001-05-20 | Abbott Lab | 6-o-alkyl derivatives of erythronolide b |
| ES2219000T3 (es) | 1998-03-26 | 2004-11-16 | Fujisawa Pharmaceutical Co., Ltd. | Preparacion de liberacion sostenida de un compuesto macrolido. |
| 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 |
| US6387885B1 (en) | 1998-08-26 | 2002-05-14 | Abbott Laboratories | 3′,3′-N-bis-desmethyl-3′-N-cycloalkyl erythromycin derivatives as LHRH antagonists |
| US6020521A (en) | 1998-08-26 | 2000-02-01 | Abbott Laboratories | Macrolide 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 |
| KR100317907B1 (ko) | 1998-11-24 | 2001-12-24 | 김 완 주 | 신규한 중간체, 이를 이용한 마크로라이드계 항생제의제조방법 |
| 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 |
| TR200102129T2 (tr) | 1998-12-10 | 2002-01-21 | Pfizer Products Inc. | Karbamat ve karbazat ketolid antibiyotikleri. |
| KR20020002380A (ko) | 1999-01-27 | 2002-01-09 | 실버스타인 아써 에이. | 케톨라이드 항생물질 |
| 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 |
| AR023264A1 (es) | 1999-04-08 | 2002-09-04 | Hokuriku Pharmaceutical | Derivados de eritromicina |
| JP2000351794A (ja) | 1999-04-08 | 2000-12-19 | Hokuriku Seiyaku Co Ltd | エリスロマイシン誘導体 |
| ATE340183T1 (de) | 1999-04-16 | 2006-10-15 | Kosan Biosciences Inc | Antiinfektiöse makrolidderivate |
| CN1373767A (zh) | 1999-04-16 | 2002-10-09 | 奥索-麦克尼尔药品公司 | 酮式大环内酯抗菌剂 |
| 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 |
| 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 |
| WO2001068662A1 (en) | 2000-03-15 | 2001-09-20 | Hanmi Pharm. Co., Ltd. | Method of preparing clarithromycin of form ii crystals |
| 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 |
| ES2261735T3 (es) | 2001-05-18 | 2006-11-16 | Chiron Corporation | Sistema para la administracion de una formulacion de tobramicina. |
| JP4509553B2 (ja) | 2001-07-03 | 2010-07-21 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | 抗菌活性を有するｃ１２修飾エリスロマイシンマクロライドおよびケトライド |
| US20030176327A1 (en) | 2001-10-25 | 2003-09-18 | Cassell Gail Houston | Antibiotics for treating biohazardous bacterial agents |
| MXPA04008173A (es) | 2002-02-22 | 2004-11-26 | Pharmacia Corp | Formulaciones de farmaco antibiotico oftalmico que contienen un compuesto de ciclodextrina y cloruro de cetil piridinio. |
| DK2226316T3 (en) | 2002-05-30 | 2016-04-11 | Scripps Research Inst | Copper catalyzed ligation of azides and acetylenes |
| IL165291A0 (en) | 2002-06-17 | 2005-12-18 | Epigenesis Pharmaceuticals Llc | Dihydrate dehydroepiandorosterone 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. |
| EP1638549A4 (en) | 2003-03-10 | 2011-06-15 | Optimer Pharmaceuticals Inc | NEW ANTIBACTERIAL AGENTS |
| CA2523134A1 (en) | 2003-04-25 | 2004-11-11 | Chiron Corporation | Pyridyl substituted ketolide antibiotics |
| EP1618120A2 (en) * | 2003-04-25 | 2006-01-25 | Chiron Corporation | Novel ketolide derivatives |
| HRP20070094T3 (hr) | 2003-05-13 | 2008-05-31 | Glaxo Group Limited | NOVI 14- i 15-EROČLANI PRSTENASTI SPOJEVI |
| 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 |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| US20060116336A1 (en) | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| EP1742957B1 (en) | 2004-04-28 | 2007-09-12 | Alembic Limited | Process for the preparation of telithromycin |
| ES2331739T3 (es) | 2004-05-06 | 2010-01-14 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Macrolidos que contienen enlaces ester utiles para el tratamiento de infecciones microbianas. |
| BRPI0513903A (pt) | 2004-07-28 | 2008-05-20 | Ranbaxy Lab Ltd | derivados de cetolìdeos úteis como agentes antimicrobianos, seus processos de preparação e composições farmacêuticas compreendendo os mesmos |
| GB0424959D0 (en) | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424958D0 (en) | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| DE602006006546D1 (de) | 2005-01-14 | 2009-06-10 | Glaxosmithkline Zagreb | 9a-carbamoyl- und thiocarbamoylazalide mit antimalariawirkung |
| EP1836212B1 (en) | 2005-01-14 | 2011-09-07 | Glaxo Group Limited | Macrolide compounds containing biotin and photo-affinity group for macrolide target identification |
| WO2006075256A2 (en) | 2005-01-14 | 2006-07-20 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | 9a-carbamoyl-ϝ-aminopropyl- and 9a-thiocarbamoyl-ϝ-aminopropyl-azalides with antimalarial activity |
| 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 |
| AU2006270039B2 (en) | 2005-07-19 | 2013-07-04 | Azevan Pharmaceuticals, Inc. | Beta-lactamyl phenylalanine, cysteine, and serine vasopressin antagonists |
| EP1957085A2 (en) * | 2005-11-08 | 2008-08-20 | Ranbaxy Laboratories, Ltd. | Macrolides as anti-inflammatory agents |
| WO2007059307A2 (en) | 2005-11-15 | 2007-05-24 | Teva Pharmaceutical Industries Ltd. | Crystalline and amorphous forms of telithromycin |
| US20090075916A1 (en) * | 2005-11-23 | 2009-03-19 | Upadhyay Dilip J | Use of Macrolide Derivatives for Treating Acne |
| EP1957508A2 (en) * | 2005-11-23 | 2008-08-20 | Ranbaxy Laboratories Limited | Ketolide derivatives as antibacterial agents |
| US20090130225A1 (en) * | 2005-11-23 | 2009-05-21 | Anjan Chakrabarti | Macrolides derivatives as antibacterial agents |
| 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 |
| US8124744B2 (en) | 2006-05-01 | 2012-02-28 | Taisho Pharmaceutical Co., Ltd. | Macrolide derivatives |
| EP2023721A2 (en) | 2006-06-05 | 2009-02-18 | Auspex Pharmaceuticals Inc. | Preparation and utility of substituted erythromycin analogs |
| 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 |
| US9453042B2 (en) | 2007-10-25 | 2016-09-27 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| HRP20160222T1 (hr) | 2008-10-24 | 2016-04-08 | Cempra Pharmaceuticals, Inc. | Biozaštite uporabom makrolida koji sadrže triazol |
| US9814657B2 (en) | 2009-04-27 | 2017-11-14 | Premier Dental Products Company | Buffered microencapsulated compositions and methods |
| CA2767614C (en) | 2009-07-13 | 2019-01-15 | 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 |
| ES2637072T3 (es) | 2010-03-10 | 2017-10-10 | Cempra Pharmaceuticals, Inc. | Formulación parenteral de antibióticos macrólidos |
| 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 |
| CN102917708B (zh) | 2010-05-20 | 2015-11-25 | 森普拉制药公司 | 制备大环内酯和酮内酯及其中间体的方法 |
| US8247394B2 (en) | 2010-06-02 | 2012-08-21 | Cempra Pharmaceuticals Inc. | Methods of treating urethritis and related infections using fusidic acid |
| WO2012012257A2 (en) | 2010-07-19 | 2012-01-26 | Virginia Commonwealth University | BIVALENT MULTIFUNCTIONAL LIGANDS TARGETING Aβ OLIGOMERS AS TREATMENT FOR ALZHEIMER'S DISEASE |
| CA2812044A1 (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 |
| KR101512738B1 (ko) | 2011-08-27 | 2015-04-17 | 욱크하르트 리미티드 | 1,6-디아자-비시클로[3,2,1]옥탄-7-온 유도체 및 세균 감염 치료에서의 그 유도체의 용도 |
| AR091790A1 (es) | 2011-08-29 | 2015-03-04 | Infinity Pharmaceuticals Inc | Derivados de isoquinolin-1-ona y sus usos |
| IN2014DN08939A (enExample) | 2012-03-27 | 2015-05-22 | Cempra Pharmaceuticals Inc | |
| CA2905975A1 (en) | 2013-03-14 | 2014-09-25 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| EP2968384A4 (en) | 2013-03-15 | 2017-02-15 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| MX377459B (es) | 2013-04-04 | 2025-03-10 | Harvard College | Macrolidos y metodos para su preparacion y uso. |
| CN106660945A (zh) | 2014-05-27 | 2017-05-10 | 迪法玛弗朗西斯有限公司 | 叠氮基烷基胺盐及其作为中间体的用途 |
-
2011
- 2011-09-09 US US13/821,314 patent/US9815863B2/en not_active Expired - Fee Related
- 2011-09-09 KR KR1020187027659A patent/KR20180110181A/ko not_active Ceased
- 2011-09-09 JP JP2013528344A patent/JP6042334B2/ja active Active
- 2011-09-09 WO PCT/US2011/051064 patent/WO2012034058A1/en not_active Ceased
- 2011-09-09 EP EP11824199.1A patent/EP2613630A4/en not_active Withdrawn
- 2011-09-09 KR KR1020137009177A patent/KR20130120458A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20130172280A1 (en) | 2013-07-04 |
| JP2013537198A (ja) | 2013-09-30 |
| JP6042334B2 (ja) | 2016-12-14 |
| KR20130120458A (ko) | 2013-11-04 |
| EP2613630A1 (en) | 2013-07-17 |
| WO2012034058A1 (en) | 2012-03-15 |
| EP2613630A4 (en) | 2014-01-15 |
| US9815863B2 (en) | 2017-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20180110181A (ko) | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 | |
| Poulsen et al. | Inhibition of the ribosomal peptidyl transferase reaction by the mycarose moiety of the antibiotics carbomycin, spiramycin and tylosin | |
| JP3140703B2 (ja) | 新規なエリスロマイシン、それらの製造法及び薬剤としての用途 | |
| CZ298556B6 (cs) | Derivát 4"-substituovaného-9-deoxo-9a-aza-9a-homoerythromycinu, zpusob a meziprodukty pro jeho prípravu a farmaceutické kompozice s jeho obsahem | |
| CA2956465A1 (en) | Cyclohexyl-ethyl substituted diaza- and triaza-tricyclic compounds as indole-amine-2,3-dioxygenase (ido) antagonists for the treatment of cancer | |
| JP2011006474A (ja) | 新規な非ステロイド抗炎症物質、組成物、およびその使用方法 | |
| JP2011136990A (ja) | 新規のエリスロマイシン誘導体、それらの製造方法及びそれらの薬剤としての使用 | |
| BG63207B1 (bg) | Нови производни на еритромицин, метод за тяхното получаване и използването им като лекарствено средство | |
| CZ300063B6 (cs) | Ketolidové deriváty, zpusob jejich prípravy, jejich použití a farmaceutické kompozice s jejich obsahem | |
| CA3169676A1 (en) | Compounds and methods for modulating splicing | |
| JP2000159790A (ja) | 新規のエリスロマイシン誘導体、それらの製造方法及びそれらの薬剤としての使用 | |
| Magee et al. | Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections | |
| CA3169697A1 (en) | Thiophenyl derivatives useful for modulating nucleic acid splicing | |
| Bertho et al. | Transferred nuclear Overhauser effect study of macrolide–ribosome interactions: correlation between antibiotic activities and bound conformations | |
| CN114437154B (zh) | 一种含有喹诺酮的酮内酯衍生物及其制备方法和应用 | |
| CA3239110A1 (en) | Compounds and methods for modulating splicing | |
| Murphy-Benenato et al. | Identification through structure-based methods of a bacterial NAD+-dependent DNA ligase inhibitor that avoids known resistance mutations | |
| ES2392860T3 (es) | Compuestos motílidos | |
| Dinos et al. | Erythromycin, roxithromycin, and clarithromycin: use of slow-binding kinetics to compare their in vitro interaction with a bacterial ribosomal complex active in peptide bond formation | |
| Durcik et al. | Benzothiazole DNA gyrase inhibitors and their conjugates with siderophore mimics: design, synthesis and evaluation | |
| NZ231722A (en) | Amphotericin beta derivatives, pharmaceutical compositions and preparation thereof | |
| EP3719020B1 (en) | Crystal form of beta-lactamase inhibitor and preparation method therefor | |
| EP0507595A1 (en) | 8A-aza-8A-homoerythromycin lactams | |
| WO2019094631A1 (en) | Compounds and methods for treating bacterial infections | |
| WO2016210239A1 (en) | Methods of identifying novel antibiotics using in situ click chemistry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20180921 Application number text: 1020137009177 Filing date: 20130410 |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20181019 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20181026 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20190319 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20181026 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |