NL2000373C2 - Antibacteriële middelen. - Google Patents

Info

Publication number

NL2000373C2

NL2000373C2 NL2000373A NL2000373A NL2000373C2 NL 2000373 C2 NL2000373 C2 NL 2000373C2 NL 2000373 A NL2000373 A NL 2000373A NL 2000373 A NL2000373 A NL 2000373A NL 2000373 C2 NL2000373 C2 NL 2000373C2

Authority

NL

Netherlands

Prior art keywords

compound

substituted

dimethyl

unsubstituted

tetrahydro

Prior art date

2005-12-22

Links

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• 239000003242 anti bacterial agent Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 215
• -1 morpholin-4-yl-methyl Chemical group 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 83
• 238000006243 chemical reaction Methods 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 41
• 238000000034 method Methods 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 28
• 150000002170 ethers Chemical class 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• 238000005859 coupling reaction Methods 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000003960 organic solvent Substances 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 230000008878 coupling Effects 0.000 claims description 11
• 238000010168 coupling process Methods 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 239000000651 prodrug Substances 0.000 claims description 10
• 229940002612 prodrug Drugs 0.000 claims description 10
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 241000894006 Bacteria Species 0.000 claims description 8
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 238000009833 condensation Methods 0.000 claims description 8
• 230000005494 condensation Effects 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 8
• 208000035143 Bacterial infection Diseases 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 230000000844 anti-bacterial effect Effects 0.000 claims description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 150000007529 inorganic bases Chemical class 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 150000003216 pyrazines Chemical class 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000000539 amino acid group Chemical group 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 150000007530 organic bases Chemical class 0.000 claims description 6
• 108090000765 processed proteins & peptides Chemical group 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 claims description 4
• 238000010537 deprotonation reaction Methods 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 4
• 229910052744 lithium Inorganic materials 0.000 claims description 4
• 239000007818 Grignard reagent Substances 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 3
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
• 150000004795 grignard reagents Chemical class 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 229910052751 metal Inorganic materials 0.000 claims description 3
• 239000002184 metal Substances 0.000 claims description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
• 230000001590 oxidative effect Effects 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 2
• 125000005997 bromomethyl group Chemical group 0.000 claims description 2
• 230000003647 oxidation Effects 0.000 claims description 2
• 238000007254 oxidation reaction Methods 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims 5
• HXWBOBUFJUFVLC-UHFFFAOYSA-N spiro[4H-pyrimidine-5,5'-6H-[1,4]oxazino[4,3-a]quinoline] Chemical compound N=1C=NCC2(C=1)C=1N(C3=CC=CC=C3C2)C=COC=1 HXWBOBUFJUFVLC-UHFFFAOYSA-N 0.000 claims 5
• 229910019142 PO4 Inorganic materials 0.000 claims 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
• 239000010452 phosphate Substances 0.000 claims 2
• SSQYBZNZBNXQNO-LIBAHTEVSA-N (2'r,4's,4'as)-9',10'-difluoro-2',4'-dimethyl-8'-(5-methylpyrazin-2-yl)spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC(C)=NC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O SSQYBZNZBNXQNO-LIBAHTEVSA-N 0.000 claims 1
• VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims 1
• WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 claims 1
• YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 claims 1
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 230000003385 bacteriostatic effect Effects 0.000 claims 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
• 239000011541 reaction mixture Substances 0.000 description 77
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
• 235000019439 ethyl acetate Nutrition 0.000 description 64
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
• 239000007787 solid Substances 0.000 description 46
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 44
• 239000000047 product Substances 0.000 description 37
• 239000000243 solution Substances 0.000 description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
• 239000000725 suspension Substances 0.000 description 25
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• 239000000460 chlorine Substances 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 125000003118 aryl group Chemical group 0.000 description 20
• 238000004440 column chromatography Methods 0.000 description 20
• 125000004430 oxygen atom Chemical group O* 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• 239000003921 oil Substances 0.000 description 19
• 235000019198 oils Nutrition 0.000 description 19
• 238000012360 testing method Methods 0.000 description 19
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
• 238000004458 analytical method Methods 0.000 description 18
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 16
• 239000002244 precipitate Substances 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• 208000015181 infectious disease Diseases 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• 235000001014 amino acid Nutrition 0.000 description 13
• 229940024606 amino acid Drugs 0.000 description 13
• 150000001413 amino acids Chemical class 0.000 description 13
• 125000004434 sulfur atom Chemical group 0.000 description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 12
• 125000003545 alkoxy group Chemical group 0.000 description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
• 239000002002 slurry Substances 0.000 description 12
• 229910000029 sodium carbonate Inorganic materials 0.000 description 12
• 235000017550 sodium carbonate Nutrition 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 229940079593 drug Drugs 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 239000012043 crude product Substances 0.000 description 10
• 239000000284 extract Substances 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• 125000005843 halogen group Chemical group 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 238000010790 dilution Methods 0.000 description 9
• 239000012895 dilution Substances 0.000 description 9
• 238000002347 injection Methods 0.000 description 9
• 239000007924 injection Substances 0.000 description 9
• 229910052740 iodine Inorganic materials 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 229910052786 argon Inorganic materials 0.000 description 8
• 230000001580 bacterial effect Effects 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000011630 iodine Substances 0.000 description 8
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 125000005842 heteroatom Chemical group 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• 125000003003 spiro group Chemical group 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• 125000004103 aminoalkyl group Chemical group 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 125000000753 cycloalkyl group Chemical group 0.000 description 6
• 150000002430 hydrocarbons Chemical class 0.000 description 6
• 235000011056 potassium acetate Nutrition 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 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 6
• BHTGAQKPXNYOJG-UHFFFAOYSA-N 2-(2,6-dimethylmorpholin-4-yl)-3,4-difluoro-5-pyrazin-2-ylbenzaldehyde Chemical compound C1C(C)OC(C)CN1C1=C(C=O)C=C(C=2N=CC=NC=2)C(F)=C1F BHTGAQKPXNYOJG-UHFFFAOYSA-N 0.000 description 5
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 125000000304 alkynyl group Chemical group 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 229940125782 compound 2 Drugs 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 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
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 125000003373 pyrazinyl group Chemical group 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• OYWPFIUVDKHHGQ-UHFFFAOYSA-N 2-iodopyrazine Chemical compound IC1=CN=CC=N1 OYWPFIUVDKHHGQ-UHFFFAOYSA-N 0.000 description 4
• ZEKMMJFJVSCFLO-UHFFFAOYSA-N 5-bromo-2-(2,6-dimethylmorpholin-4-yl)-3,4-difluorobenzaldehyde Chemical compound C1C(C)OC(C)CN1C1=C(F)C(F)=C(Br)C=C1C=O ZEKMMJFJVSCFLO-UHFFFAOYSA-N 0.000 description 4
• 229920001817 Agar Polymers 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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• 241000606790 Haemophilus Species 0.000 description 4
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• 239000008272 agar Substances 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 229910000024 caesium carbonate Inorganic materials 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 230000012010 growth Effects 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 239000012452 mother liquor Substances 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 229910000160 potassium phosphate Inorganic materials 0.000 description 4
• 235000011009 potassium phosphates Nutrition 0.000 description 4
• 238000011321 prophylaxis Methods 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 241000894007 species Species 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
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