AU2023255378A1

AU2023255378A1 - Lincosamides and uses thereof

Lincosamides and uses thereof Download PDF

Info

Publication number: AU2023255378A1
Authority: AU; Australia
Prior art keywords: compound; substituted; unsubstituted; pharmaceutically acceptable; acceptable salt
Prior art date: 2022-04-20
Legal status : Pending

Application number

AU2023255378A

Other languages

English (en)

Inventor

Andrew G. Myers

Ben Calhoun TRESCO

Kelvin Wu

Current Assignee

Harvard University

Original Assignee

Harvard University

Priority date

2022-04-20

Filing date

2023-04-19

Publication date

2024-11-07

2023-04-19 Application filed by Harvard University filed Critical Harvard University

2024-11-07 Publication of AU2023255378A1 publication Critical patent/AU2023255378A1/en

Status Pending legal-status Critical Current

Links

229940041028 lincosamides Drugs 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims abstract description 491
238000000034 method Methods 0.000 claims abstract description 59
208000035473 Communicable disease Diseases 0.000 claims abstract description 36
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 224
150000003839 salts Chemical class 0.000 claims description 210
125000000217 alkyl group Chemical group 0.000 claims description 166
125000004452 carbocyclyl group Chemical group 0.000 claims description 105
125000005842 heteroatom Chemical group 0.000 claims description 95
229910052739 hydrogen Inorganic materials 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 88
125000003118 aryl group Chemical group 0.000 claims description 85
125000001072 heteroaryl group Chemical group 0.000 claims description 85
125000000304 alkynyl group Chemical group 0.000 claims description 84
125000003342 alkenyl group Chemical group 0.000 claims description 80
208000015181 infectious disease Diseases 0.000 claims description 78
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
229910052736 halogen Inorganic materials 0.000 claims description 51
150000002367 halogens Chemical class 0.000 claims description 51
241000894006 Bacteria Species 0.000 claims description 47
229910052757 nitrogen Inorganic materials 0.000 claims description 46
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 39
125000004404 heteroalkyl group Chemical group 0.000 claims description 36
229910052717 sulfur Inorganic materials 0.000 claims description 35
229910052760 oxygen Inorganic materials 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
208000035143 Bacterial infection Diseases 0.000 claims description 27
208000022362 bacterial infectious disease Diseases 0.000 claims description 27
239000001301 oxygen Substances 0.000 claims description 26
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000003710 aryl alkyl group Chemical group 0.000 claims description 21
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 16
125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
244000005700 microbiome Species 0.000 claims description 11
241000193163 Clostridioides difficile Species 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
241000192125 Firmicutes Species 0.000 claims description 9
229910004749 OS(O)2 Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
241000191940 Staphylococcus Species 0.000 claims description 8
125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
241000194017 Streptococcus Species 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
241000194033 Enterococcus Species 0.000 claims description 6
206010061126 Escherichia infection Diseases 0.000 claims description 5
206010061259 Klebsiella infection Diseases 0.000 claims description 5
208000032536 Pseudomonas Infections Diseases 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
206010061190 Haemophilus infection Diseases 0.000 claims description 4
208000030852 Parasitic disease Diseases 0.000 claims description 4
208000037384 Clostridium Infections Diseases 0.000 claims description 3
206010062212 Neisseria infection Diseases 0.000 claims description 2
230000002147 killing effect Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 11
241000421809 Brisaster fragilis Species 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 15
150000001413 amino acids Chemical class 0.000 abstract description 3
230000002265 prevention Effects 0.000 abstract description 3
-1 methyl thioglycoside Chemical class 0.000 description 421
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 166
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 145
239000000047 product Substances 0.000 description 142
238000005160 1H NMR spectroscopy Methods 0.000 description 131
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 126
238000000132 electrospray ionisation Methods 0.000 description 125
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 121
239000000243 solution Substances 0.000 description 109
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239000011541 reaction mixture Substances 0.000 description 94
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
238000006243 chemical reaction Methods 0.000 description 80
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 78
235000019253 formic acid Nutrition 0.000 description 73
235000019439 ethyl acetate Nutrition 0.000 description 68
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 48
239000010410 layer Substances 0.000 description 43
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 37
229910052938 sodium sulfate Inorganic materials 0.000 description 37
235000011152 sodium sulphate Nutrition 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
238000003818 flash chromatography Methods 0.000 description 32
238000002953 preparative HPLC Methods 0.000 description 32
238000000746 purification Methods 0.000 description 31
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
125000001424 substituent group Chemical group 0.000 description 30
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 28
239000003153 chemical reaction reagent Substances 0.000 description 28
125000001153 fluoro group Chemical group F* 0.000 description 28
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 28
229910000041 hydrogen chloride Inorganic materials 0.000 description 28
230000002829 reductive effect Effects 0.000 description 28
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
238000005859 coupling reaction Methods 0.000 description 25
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
230000004968 inflammatory condition Effects 0.000 description 24
229920006395 saturated elastomer Polymers 0.000 description 24
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
239000007821 HATU Substances 0.000 description 22
230000008878 coupling Effects 0.000 description 21
238000010168 coupling process Methods 0.000 description 21
125000000753 cycloalkyl group Chemical group 0.000 description 21
239000000725 suspension Substances 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
150000001408 amides Chemical class 0.000 description 19
239000011593 sulfur Substances 0.000 description 19
239000003054 catalyst Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 17
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
125000001188 haloalkyl group Chemical group 0.000 description 15
150000002772 monosaccharides Chemical class 0.000 description 15
238000010992 reflux Methods 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
125000001425 triazolyl group Chemical group 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
125000004122 cyclic group Chemical group 0.000 description 14
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 14
230000001717 pathogenic effect Effects 0.000 description 14
239000012453 solvate Substances 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 13
238000004293 19F NMR spectroscopy Methods 0.000 description 13
239000003242 anti bacterial agent Substances 0.000 description 13
239000000284 extract Substances 0.000 description 13
244000052769 pathogen Species 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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235000000346 sugar Nutrition 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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125000006163 5-membered heteroaryl group Chemical group 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
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229940088710 antibiotic agent Drugs 0.000 description 10
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KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
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235000019198 oils Nutrition 0.000 description 10
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 9
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 9
150000001720 carbohydrates Chemical class 0.000 description 9
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
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125000004429 atom Chemical group 0.000 description 7
239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
229940002612 prodrug Drugs 0.000 description 7
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 6
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 6
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 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
241000233866 Fungi Species 0.000 description 6
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230000003115 biocidal effect Effects 0.000 description 6
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125000000392 cycloalkenyl group Chemical group 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001841 imino group Chemical group [H]N=* 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
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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 5
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
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125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 4
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