CA2892027A1 - Macrocyclic broad spectrum antibiotics - Google Patents
Macrocyclic broad spectrum antibiotics Download PDFInfo
- Publication number
- CA2892027A1 CA2892027A1 CA2892027A CA2892027A CA2892027A1 CA 2892027 A1 CA2892027 A1 CA 2892027A1 CA 2892027 A CA2892027 A CA 2892027A CA 2892027 A CA2892027 A CA 2892027A CA 2892027 A1 CA2892027 A1 CA 2892027A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- alkyl
- optionally substituted
- independently
- 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.)
- Abandoned
Links
- 239000003242 anti bacterial agent Substances 0.000 title description 7
- 229940088710 antibiotic agent Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 1110
- 241000894006 Bacteria Species 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 473
- -1 cyano, hydroxy Chemical group 0.000 claims description 281
- 125000001072 heteroaryl group Chemical group 0.000 claims description 257
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 224
- 125000003118 aryl group Chemical group 0.000 claims description 186
- 125000004432 carbon atom Chemical group C* 0.000 claims description 181
- 125000000623 heterocyclic group Chemical group 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 158
- 150000001408 amides Chemical class 0.000 claims description 139
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 139
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 138
- 239000001257 hydrogen Substances 0.000 claims description 138
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 130
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 96
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 90
- 229910052799 carbon Inorganic materials 0.000 claims description 85
- 125000003107 substituted aryl group Chemical group 0.000 claims description 83
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 79
- 229910052796 boron Inorganic materials 0.000 claims description 73
- 150000002431 hydrogen Chemical class 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 69
- 239000004202 carbamide Substances 0.000 claims description 66
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 60
- 125000003342 alkenyl group Chemical group 0.000 claims description 57
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 55
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- 229940002612 prodrug Drugs 0.000 claims description 43
- 239000000651 prodrug Substances 0.000 claims description 43
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 40
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 239000012453 solvate Substances 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 239000003814 drug Substances 0.000 claims description 32
- 150000001721 carbon Chemical group 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
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- 229910052801 chlorine Inorganic materials 0.000 claims description 26
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- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052740 iodine Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 241000191967 Staphylococcus aureus Species 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
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- 125000005309 thioalkoxy group Chemical group 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 230000004962 physiological condition Effects 0.000 claims description 17
- 230000003115 biocidal effect Effects 0.000 claims description 16
- 125000003051 glycosyloxy group Chemical group 0.000 claims description 16
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 15
- 229930186147 Cephalosporin Natural products 0.000 claims description 15
- 229940124587 cephalosporin Drugs 0.000 claims description 15
- 150000001780 cephalosporins Chemical class 0.000 claims description 15
- 229940124597 therapeutic agent Drugs 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- 241000606125 Bacteroides Species 0.000 claims description 8
- 230000009286 beneficial effect Effects 0.000 claims description 8
- 241000194031 Enterococcus faecium Species 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 6
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- 241000588724 Escherichia coli Species 0.000 claims description 5
- 229930182555 Penicillin Natural products 0.000 claims description 5
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- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 5
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- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 5
- 239000002207 metabolite Substances 0.000 claims description 5
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims description 4
- 241000588626 Acinetobacter baumannii Species 0.000 claims description 4
- 241000588624 Acinetobacter calcoaceticus Species 0.000 claims description 4
- 241001148231 Acinetobacter haemolyticus Species 0.000 claims description 4
- 241000607528 Aeromonas hydrophila Species 0.000 claims description 4
- 108010001478 Bacitracin Proteins 0.000 claims description 4
- 241001135322 Bacteroides eggerthii Species 0.000 claims description 4
- 241000606124 Bacteroides fragilis Species 0.000 claims description 4
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 claims description 4
- 241000606219 Bacteroides uniformis Species 0.000 claims description 4
- 241000606215 Bacteroides vulgatus Species 0.000 claims description 4
- 241000588779 Bordetella bronchiseptica Species 0.000 claims description 4
- 241000588780 Bordetella parapertussis Species 0.000 claims description 4
- 241000588832 Bordetella pertussis Species 0.000 claims description 4
- 241000589969 Borreliella burgdorferi Species 0.000 claims description 4
- 241000589513 Burkholderia cepacia Species 0.000 claims description 4
- 241000589877 Campylobacter coli Species 0.000 claims description 4
- 241000589874 Campylobacter fetus Species 0.000 claims description 4
- 241000589875 Campylobacter jejuni Species 0.000 claims description 4
- 241000588919 Citrobacter freundii Species 0.000 claims description 4
- 241000193163 Clostridioides difficile Species 0.000 claims description 4
- 108010078777 Colistin Proteins 0.000 claims description 4
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims description 4
- 241000918600 Corynebacterium ulcerans Species 0.000 claims description 4
- 108010013198 Daptomycin Proteins 0.000 claims description 4
- 241001600125 Delftia acidovorans Species 0.000 claims description 4
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- 241000589602 Francisella tularensis Species 0.000 claims description 4
- 241000207201 Gardnerella vaginalis Species 0.000 claims description 4
- 241000606788 Haemophilus haemolyticus Species 0.000 claims description 4
- 241000606768 Haemophilus influenzae Species 0.000 claims description 4
- 241000606822 Haemophilus parahaemolyticus Species 0.000 claims description 4
- 241000606766 Haemophilus parainfluenzae Species 0.000 claims description 4
- 241000590002 Helicobacter pylori Species 0.000 claims description 4
- 241001454354 Kingella Species 0.000 claims description 4
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 4
- 241000588749 Klebsiella oxytoca Species 0.000 claims description 4
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- 241000186779 Listeria monocytogenes Species 0.000 claims description 4
- 241001293418 Mannheimia haemolytica Species 0.000 claims description 4
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- 241000588621 Moraxella Species 0.000 claims description 4
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 4
- 241000588772 Morganella morganii Species 0.000 claims description 4
- 241000186367 Mycobacterium avium Species 0.000 claims description 4
- 241000186364 Mycobacterium intracellulare Species 0.000 claims description 4
- 241000186362 Mycobacterium leprae Species 0.000 claims description 4
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 4
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims description 4
- 241000588650 Neisseria meningitidis Species 0.000 claims description 4
- 241001135232 Odoribacter splanchnicus Species 0.000 claims description 4
- 241000606210 Parabacteroides distasonis Species 0.000 claims description 4
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- 241000588777 Providencia rettgeri Species 0.000 claims description 4
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- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
- 241000168225 Pseudomonas alcaligenes Species 0.000 claims description 4
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- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 claims description 4
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 claims description 4
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims description 4
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 4
- 241000607715 Serratia marcescens Species 0.000 claims description 4
- 241000607764 Shigella dysenteriae Species 0.000 claims description 4
- 241000607762 Shigella flexneri Species 0.000 claims description 4
- 241000607760 Shigella sonnei Species 0.000 claims description 4
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- 241001464905 Staphylococcus saccharolyticus Species 0.000 claims description 4
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- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims description 4
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 4
- 229960003071 bacitracin Drugs 0.000 claims description 4
- 229930184125 bacitracin Natural products 0.000 claims description 4
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims description 4
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- DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical compound C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 claims description 4
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- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 claims description 4
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- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1019—Tetrapeptides with the first amino acid being basic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261729253P | 2012-11-21 | 2012-11-21 | |
| US201261729249P | 2012-11-21 | 2012-11-21 | |
| US61/729,249 | 2012-11-21 | ||
| US61/729,253 | 2012-11-21 | ||
| PCT/US2013/071093 WO2014081886A1 (en) | 2012-11-21 | 2013-11-20 | Macrocyclic broad spectrum antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2892027A1 true CA2892027A1 (en) | 2014-05-30 |
Family
ID=50728492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2892027A Abandoned CA2892027A1 (en) | 2012-11-21 | 2013-11-20 | Macrocyclic broad spectrum antibiotics |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9309285B2 (OSRAM) |
| EP (1) | EP2922829B1 (OSRAM) |
| JP (2) | JP6437443B2 (OSRAM) |
| KR (1) | KR20150088292A (OSRAM) |
| CN (1) | CN104903302B (OSRAM) |
| AR (1) | AR093581A1 (OSRAM) |
| BR (1) | BR112015011697A2 (OSRAM) |
| CA (1) | CA2892027A1 (OSRAM) |
| EA (1) | EA201590871A1 (OSRAM) |
| MX (1) | MX2015006340A (OSRAM) |
| TW (1) | TWI631127B (OSRAM) |
| WO (1) | WO2014081886A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| KR102346455B1 (ko) | 2013-03-15 | 2022-01-04 | 더 트러스티스 오브 더 유니버시티 오브 펜실베니아 | Ｍｐｓｉ 치료를 위한 조성물 및 방법 |
| RU2016146581A (ru) * | 2014-05-20 | 2018-06-21 | АрКьюЭкс ФАРМАСЪЮТИКЛС, ИНК. | Макроциклические антибиотики широкого спектра действия |
| AU2016254226C1 (en) * | 2015-04-30 | 2022-11-24 | Idexx Laboratories, Inc. | Methods for detecting renal disease |
| CR20180232A (es) | 2015-10-27 | 2018-05-31 | Hoffmann La Roche | Macrociclos peptídicos contra acinetobacter baumannii |
| EP3377474B1 (en) * | 2015-11-20 | 2023-08-16 | RQX Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| TWI725075B (zh) * | 2015-11-20 | 2021-04-21 | 美商Ｒｑｘ製藥公司 | 巨環廣效抗生素 |
| IL268483B2 (en) * | 2017-02-15 | 2024-02-01 | Rqx Pharmaceuticals Inc | Macrocyclic broad spectrum antibiotics |
| EP3388444A1 (en) | 2017-04-10 | 2018-10-17 | F. Hoffmann-La Roche AG | Anti-bacterial peptide macrocycles and use thereof |
| US11505573B2 (en) | 2018-03-28 | 2022-11-22 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| US11819532B2 (en) | 2018-04-23 | 2023-11-21 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| IL295889B2 (en) * | 2019-05-28 | 2025-01-01 | Hoffmann La Roche | Broad-spectrum macrocyclic antibiotic |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5204328A (en) | 1990-06-26 | 1993-04-20 | Merck & Co., Inc. | Peptides having atrial natriuretic factor activity |
| EP0895999A1 (en) * | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| US6660832B1 (en) * | 1999-08-20 | 2003-12-09 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds and preparation methods thereof |
| US6951840B2 (en) * | 2001-08-31 | 2005-10-04 | Eli Lilly And Company | Lipoglycopeptide antibiotics |
| DE10226921A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Antibakterielle Amid-Makrozyklen |
| CA2530063A1 (en) | 2003-06-26 | 2005-01-06 | Migenix Inc. | Compositions of lipopeptide antibiotic derivatives and methods of use thereof |
| DE10358824A1 (de) * | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005014245A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen V |
| DE102005014247A1 (de) * | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen VI |
| BR112012021931A2 (pt) * | 2010-03-09 | 2016-05-31 | Merck Canada Inc | composto, composição farmacêutica, método para tratar uma infecção bacteriana, e, uso de composto |
| WO2011120071A1 (en) | 2010-04-01 | 2011-10-06 | The University Of Queensland | Oxytocin peptide analogues |
| KR20130105659A (ko) * | 2010-09-15 | 2013-09-25 | 더 스크립스 리서치 인스티튜트 | 광범위 스펙트럼 항생제 아릴로마이신 유사체 |
| WO2012166665A2 (en) | 2011-05-27 | 2012-12-06 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| CA2867448A1 (en) | 2012-03-14 | 2013-09-19 | Floyd E. Romesberg | Broad spectrum antibiotic arylomycin analogs |
-
2013
- 2013-11-20 CA CA2892027A patent/CA2892027A1/en not_active Abandoned
- 2013-11-20 WO PCT/US2013/071093 patent/WO2014081886A1/en not_active Ceased
- 2013-11-20 CN CN201380069987.6A patent/CN104903302B/zh active Active
- 2013-11-20 JP JP2015544117A patent/JP6437443B2/ja active Active
- 2013-11-20 EA EA201590871A patent/EA201590871A1/ru unknown
- 2013-11-20 EP EP13856377.0A patent/EP2922829B1/en active Active
- 2013-11-20 BR BR112015011697A patent/BR112015011697A2/pt not_active Application Discontinuation
- 2013-11-20 MX MX2015006340A patent/MX2015006340A/es unknown
- 2013-11-20 KR KR1020157016534A patent/KR20150088292A/ko not_active Withdrawn
- 2013-11-21 US US14/086,908 patent/US9309285B2/en active Active
- 2013-11-21 AR ARP130104303A patent/AR093581A1/es unknown
- 2013-11-21 TW TW102142527A patent/TWI631127B/zh not_active IP Right Cessation
-
2018
- 2018-07-18 JP JP2018135357A patent/JP6662960B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016501864A (ja) | 2016-01-21 |
| US20140142029A1 (en) | 2014-05-22 |
| MX2015006340A (es) | 2015-09-07 |
| AR093581A1 (es) | 2015-06-10 |
| TWI631127B (zh) | 2018-08-01 |
| CN104903302A (zh) | 2015-09-09 |
| EP2922829A4 (en) | 2016-11-02 |
| US9309285B2 (en) | 2016-04-12 |
| JP6437443B2 (ja) | 2018-12-12 |
| EA201590871A1 (ru) | 2015-11-30 |
| BR112015011697A2 (pt) | 2017-07-11 |
| EP2922829A1 (en) | 2015-09-30 |
| CN104903302B (zh) | 2019-03-29 |
| KR20150088292A (ko) | 2015-07-31 |
| TW201434848A (zh) | 2014-09-16 |
| JP2018184435A (ja) | 2018-11-22 |
| EP2922829B1 (en) | 2021-08-11 |
| WO2014081886A1 (en) | 2014-05-30 |
| JP6662960B2 (ja) | 2020-03-11 |
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| US8999922B2 (en) | Linear peptide antibiotics | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20181113 |
|
| FZDE | Discontinued |
Effective date: 20210831 |
|
| FZDE | Discontinued |
Effective date: 20210831 |