CA2487918A1 - 3-descladinosyl-6-o-carbamoyl and 6-o-carbonoyl macrolide antibacterial agents - Google Patents

Info

Publication number

CA2487918A1

CA2487918A1 CA002487918A CA2487918A CA2487918A1 CA 2487918 A1 CA2487918 A1 CA 2487918A1 CA 002487918 A CA002487918 A CA 002487918A CA 2487918 A CA2487918 A CA 2487918A CA 2487918 A1 CA2487918 A1 CA 2487918A1

Authority

CA

Canada

Prior art keywords

mmol

compound

stirred

methanol

sat

Prior art date

2002-05-31

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

• Espacenet
• Global Dossier
• CIPO
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• 239000003242 anti bacterial agent Substances 0.000 title abstract description 13
• 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 387
• 125000001424 substituent group Chemical group 0.000 claims abstract description 17
• 239000000203 mixture Substances 0.000 claims description 191
• -1 heterocyclo Chemical group 0.000 claims description 79
• 238000000034 method Methods 0.000 claims description 55
• 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 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 229960003276 erythromycin Drugs 0.000 claims description 16
• 241000894006 Bacteria Species 0.000 claims description 15
• 208000035143 Bacterial infection Diseases 0.000 claims description 13
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 239000000651 prodrug Substances 0.000 claims description 6
• 229940002612 prodrug Drugs 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 241000606768 Haemophilus influenzae Species 0.000 claims description 4
• 206010005940 Bone and joint infections Diseases 0.000 claims description 3
• 206010024971 Lower respiratory tract infections Diseases 0.000 claims description 3
• 208000032376 Lung infection Diseases 0.000 claims description 3
• 201000009906 Meningitis Diseases 0.000 claims description 3
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 3
• 206010062255 Soft tissue infection Diseases 0.000 claims description 3
• 206010046306 Upper respiratory tract infection Diseases 0.000 claims description 3
• 230000003115 biocidal effect Effects 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 244000052769 pathogen Species 0.000 claims description 3
• 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 3
• 206010040872 skin infection Diseases 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
• 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
• 230000003287 optical effect Effects 0.000 claims description 2
• 230000000241 respiratory effect Effects 0.000 claims description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 8
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
• 241001478240 Coccus Species 0.000 claims 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
• 241000194033 Enterococcus Species 0.000 claims 1
• 230000001717 pathogenic effect Effects 0.000 claims 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 813
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 528
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 376
• 239000000243 solution Substances 0.000 description 212
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 193
• 238000006243 chemical reaction Methods 0.000 description 161
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 151
• 238000004587 chromatography analysis Methods 0.000 description 148
• 239000000741 silica gel Substances 0.000 description 143
• 229910002027 silica gel Inorganic materials 0.000 description 143
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 142
• 229910017974 NH40H Inorganic materials 0.000 description 137
• 239000012267 brine Substances 0.000 description 133
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 133
• 238000000746 purification Methods 0.000 description 125
• 235000019439 ethyl acetate Nutrition 0.000 description 123
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 123
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 109
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 94
• 230000003197 catalytic effect Effects 0.000 description 82
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 62
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 60
• 229940086542 triethylamine Drugs 0.000 description 57
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 54
• 239000012043 crude product Substances 0.000 description 47
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• 238000002360 preparation method Methods 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
• 239000002904 solvent Substances 0.000 description 31
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 29
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 22
• 229910000027 potassium carbonate Inorganic materials 0.000 description 22
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 21
• LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 20
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 15
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 15
• 239000012264 purified product Substances 0.000 description 15
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 15
• WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 13
• 150000001299 aldehydes Chemical class 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• 229940125904 compound 1 Drugs 0.000 description 12
• 235000011181 potassium carbonates Nutrition 0.000 description 12
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
• 239000012442 inert solvent Substances 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 230000000844 anti-bacterial effect Effects 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• VHGYZPVCPDXGIG-UHFFFAOYSA-N 12,15-dioxa-17-azabicyclo[12.3.0]heptadeca-1,4,6,8,13-pentaene-3,11,16-trione Chemical compound O1C(=O)CC=CC=CC=CC(=O)C=C2NC(=O)OC2=C1 VHGYZPVCPDXGIG-UHFFFAOYSA-N 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 8
• 239000003054 catalyst Substances 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 230000035484 reaction time Effects 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• MQVISALTZUNQSK-UHFFFAOYSA-N 2-pyridin-2-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=N1 MQVISALTZUNQSK-UHFFFAOYSA-N 0.000 description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 150000008064 anhydrides Chemical class 0.000 description 6
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• 229930006677 Erythromycin A Natural products 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 125000002252 acyl group Chemical group 0.000 description 5
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 235000019260 propionic acid Nutrition 0.000 description 5
• RYGIHSLRMNXWCN-UHFFFAOYSA-N quinoline-3-carbaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CN=C21 RYGIHSLRMNXWCN-UHFFFAOYSA-N 0.000 description 5
• 125000006413 ring segment Chemical group 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 238000005809 transesterification reaction Methods 0.000 description 5
• XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 4
• GECTZSIHXOCIEZ-UHFFFAOYSA-N 2-formyl-4,4-dimethoxybutanenitrile Chemical compound COC(OC)CC(C=O)C#N GECTZSIHXOCIEZ-UHFFFAOYSA-N 0.000 description 4
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 4
• JUYLMPWKVWDXBE-UHFFFAOYSA-N 4-pyrimidin-2-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=NC=CC=N1 JUYLMPWKVWDXBE-UHFFFAOYSA-N 0.000 description 4
• 241000124008 Mammalia Species 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 229910003827 NRaRb Inorganic materials 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• RAXRBLLAEYLMDU-UHFFFAOYSA-N ethyl 3-(2-cyclopropylpyrimidin-5-yl)prop-2-enoate Chemical compound N1=CC(C=CC(=O)OCC)=CN=C1C1CC1 RAXRBLLAEYLMDU-UHFFFAOYSA-N 0.000 description 4
• 229950007593 homonicotinic acid Drugs 0.000 description 4
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 229910052701 rubidium Inorganic materials 0.000 description 4
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
• FRHRVQQUICVJDG-UHFFFAOYSA-M 1,3-dioxolan-2-ylmethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1OCCO1 FRHRVQQUICVJDG-UHFFFAOYSA-M 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• HATGJSYWYXYILC-UHFFFAOYSA-N 3-(2-propan-2-ylpyrimidin-5-yl)prop-2-enal Chemical compound CC(C)C1=NC=C(C=CC=O)C=N1 HATGJSYWYXYILC-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 241000943303 Enterococcus faecalis ATCC 29212 Species 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 238000005917 acylation reaction Methods 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 239000004599 antimicrobial Substances 0.000 description 3
• 150000003934 aromatic aldehydes Chemical class 0.000 description 3
• 230000001580 bacterial effect Effects 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 238000003379 elimination reaction Methods 0.000 description 3
• 230000032050 esterification Effects 0.000 description 3
• 238000005886 esterification reaction Methods 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 125000001188 haloalkyl group Chemical group 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 150000002430 hydrocarbons Chemical class 0.000 description 3
• 239000003835 ketolide antibiotic agent Substances 0.000 description 3
• 244000005700 microbiome Species 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
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