IL310280A

IL310280A - C10-cyclic substituted 13-membered macrolides and uses thereof

C10-cyclic substituted 13-membered macrolides and uses thereof

Info

Publication number: IL310280A
Authority: IL; Israel
Prior art keywords: optionally substituted; alkyl; group; compound; pharmaceutically acceptable
Prior art date: 2018-11-19

Application number

IL310280A

Other languages

English (en)

Hebrew (he)

Original Assignee

Zikani Therapeutics Inc

Harvard College

Priority date

2018-11-19

Filing date

2019-11-18

Publication date

2024-03-01

2019-11-18 Application filed by Zikani Therapeutics Inc, Harvard College filed Critical Zikani Therapeutics Inc

2024-03-01 Publication of IL310280A publication Critical patent/IL310280A/en

Links

239000003120 macrolide antibiotic agent Substances 0.000 title description 64
229940041033 macrolides Drugs 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims description 589
238000000034 method Methods 0.000 claims description 236
-1 heteroalkenyl Chemical group 0.000 claims description 206
125000005842 heteroatom Chemical group 0.000 claims description 152
150000003839 salts Chemical class 0.000 claims description 148
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 109
125000001072 heteroaryl group Chemical group 0.000 claims description 96
229910052760 oxygen Inorganic materials 0.000 claims description 86
229910052717 sulfur Inorganic materials 0.000 claims description 86
125000000217 alkyl group Chemical group 0.000 claims description 84
125000000623 heterocyclic group Chemical group 0.000 claims description 77
125000004429 atom Chemical group 0.000 claims description 75
125000005843 halogen group Chemical group 0.000 claims description 75
125000000547 substituted alkyl group Chemical group 0.000 claims description 75
125000003342 alkenyl group Chemical group 0.000 claims description 70
125000004452 carbocyclyl group Chemical group 0.000 claims description 65
208000015181 infectious disease Diseases 0.000 claims description 65
125000003118 aryl group Chemical group 0.000 claims description 60
229920006395 saturated elastomer Polymers 0.000 claims description 56
125000003545 alkoxy group Chemical group 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 46
125000004404 heteroalkyl group Chemical group 0.000 claims description 38
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
125000003107 substituted aryl group Chemical group 0.000 claims description 37
241000894006 Bacteria Species 0.000 claims description 36
208000035473 Communicable disease Diseases 0.000 claims description 35
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 30
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 30
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
208000035143 Bacterial infection Diseases 0.000 claims description 27
208000022362 bacterial infectious disease Diseases 0.000 claims description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
239000008194 pharmaceutical composition Substances 0.000 claims description 21
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 19
125000005017 substituted alkenyl group Chemical group 0.000 claims description 18
125000001188 haloalkyl group Chemical group 0.000 claims description 16
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 12
125000002393 azetidinyl group Chemical group 0.000 claims description 11
241000192125 Firmicutes Species 0.000 claims description 10
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
238000010511 deprotection reaction Methods 0.000 claims description 9
125000002950 monocyclic group Chemical group 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
125000002619 bicyclic group Chemical group 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000004069 aziridinyl group Chemical group 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([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
125000003386 piperidinyl group Chemical group 0.000 claims description 7
241000191940 Staphylococcus Species 0.000 claims description 6
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
208000030852 Parasitic disease Diseases 0.000 claims description 5
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
238000006268 reductive amination reaction Methods 0.000 claims description 5
208000034950 Acinetobacter Infections Diseases 0.000 claims description 4
206010061126 Escherichia infection Diseases 0.000 claims description 4
206010061259 Klebsiella infection Diseases 0.000 claims description 4
208000032536 Pseudomonas Infections Diseases 0.000 claims description 4
125000005275 alkylenearyl group Chemical group 0.000 claims description 4
125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
230000002152 alkylating effect Effects 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
150000004675 formic acid derivatives Chemical class 0.000 description 175
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 163
238000005481 NMR spectroscopy Methods 0.000 description 142
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 113
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 108
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
125000004432 carbon atom Chemical group C* 0.000 description 95
239000011541 reaction mixture Substances 0.000 description 89
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 65
239000000203 mixture Substances 0.000 description 58
238000005160 1H NMR spectroscopy Methods 0.000 description 57
125000000304 alkynyl group Chemical group 0.000 description 53
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 45
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 45
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 38
229910052757 nitrogen Inorganic materials 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 37
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 37
239000000543 intermediate Substances 0.000 description 35
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 34
235000019439 ethyl acetate Nutrition 0.000 description 34
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 32
125000001424 substituent group Chemical group 0.000 description 30
230000004968 inflammatory condition Effects 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
239000012044 organic layer Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
229910052938 sodium sulfate Inorganic materials 0.000 description 25
235000011152 sodium sulphate Nutrition 0.000 description 25
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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 23
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 22
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
239000003795 chemical substances by application Substances 0.000 description 22
239000007787 solid Substances 0.000 description 22
235000017557 sodium bicarbonate Nutrition 0.000 description 21
229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
235000000346 sugar Nutrition 0.000 description 20
239000002904 solvent Substances 0.000 description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 18
239000001301 oxygen Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000007832 Na2SO4 Substances 0.000 description 17
239000011593 sulfur Substances 0.000 description 17
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 16
150000001299 aldehydes Chemical class 0.000 description 16
239000012267 brine Substances 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
150000002772 monosaccharides Chemical class 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
125000004122 cyclic group Chemical group 0.000 description 14
238000004128 high performance liquid chromatography Methods 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
239000011734 sodium Substances 0.000 description 14
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
235000011114 ammonium hydroxide Nutrition 0.000 description 13
238000010828 elution Methods 0.000 description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
230000001717 pathogenic effect Effects 0.000 description 13
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 12
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 12
239000003242 anti bacterial agent Substances 0.000 description 12
244000052769 pathogen Species 0.000 description 12
239000012453 solvate Substances 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
229940088710 antibiotic agent Drugs 0.000 description 11
239000013058 crude material Substances 0.000 description 11
JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 11
235000019253 formic acid Nutrition 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
235000019270 ammonium chloride Nutrition 0.000 description 10
239000003814 drug Substances 0.000 description 10
238000005932 reductive alkylation reaction Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
125000005915 C6-C14 aryl group Chemical group 0.000 description 9
239000002253 acid Substances 0.000 description 9
150000001720 carbohydrates Chemical class 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
239000000284 extract Substances 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
230000001580 bacterial effect Effects 0.000 description 8
235000014633 carbohydrates Nutrition 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
229960003276 erythromycin Drugs 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
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 8
BACSZMCLZIDTIO-IBGZPJMESA-N n-(4-{[(3s)-3-(dimethylamino)pyrrolidin-1-yl]carbonyl}phenyl)-5-fluoro-4-[2-methyl-1-(1-methylethyl)-1h-imidazol-5-yl]pyrimidin-2-amine Chemical compound CC(C)N1C(C)=NC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)N2C[C@H](CC2)N(C)C)=NC=C1F BACSZMCLZIDTIO-IBGZPJMESA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
230000001225 therapeutic effect Effects 0.000 description 8
210000001519 tissue Anatomy 0.000 description 8
ZDXUSCQWOOIKJR-KOLCDFICSA-N (1R,2R)-1-amino-1-(1-propyl-3,6-dihydro-2H-pyridin-4-yl)propan-2-ol Chemical compound CCCN(CC1)CC=C1[C@H]([C@@H](C)O)N ZDXUSCQWOOIKJR-KOLCDFICSA-N 0.000 description 7
206010061218 Inflammation Diseases 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
230000004054 inflammatory process Effects 0.000 description 7
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 6
241000192142 Proteobacteria Species 0.000 description 6
239000008346 aqueous phase Substances 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
230000008901 benefit Effects 0.000 description 6
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
125000003367 polycyclic group Chemical group 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 description 5
HIDJWBGOQFTDLU-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical group CC(C)(C)OC(=O)NCCCC(O)=O HIDJWBGOQFTDLU-UHFFFAOYSA-N 0.000 description 5
125000006163 5-membered heteroaryl group Chemical group 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
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