OA10475A - Cyclic hexapeptides having antibiotic activity - Google Patents

Info

Publication number

OA10475A

OA10475A OA60989A OA60989A OA10475A OA 10475 A OA10475 A OA 10475A OA 60989 A OA60989 A OA 60989A OA 60989 A OA60989 A OA 60989A OA 10475 A OA10475 A OA 10475A

Authority

OA

OAPI

Prior art keywords

alkoxy

phenyl

substituted

alkyl

hâve

Prior art date

1994-10-07

Links

• Espacenet
• Global Dossier
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• 230000003115 biocidal effect Effects 0.000 title 1
• 125000004122 cyclic group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 133
• 229920001184 polypeptide Polymers 0.000 claims abstract description 14
• 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 14
• 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 14
• 238000000034 method Methods 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 524
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 310
• 125000000217 alkyl group Chemical group 0.000 claims description 272
• 125000003118 aryl group Chemical group 0.000 claims description 218
• 125000001589 carboacyl group Chemical group 0.000 claims description 209
• -1 indolylcarbonyl Chemical group 0.000 claims description 190
• 125000001424 substituent group Chemical group 0.000 claims description 144
• 125000003435 aroyl group Chemical group 0.000 claims description 116
• 125000000623 heterocyclic group Chemical group 0.000 claims description 86
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 67
• 229910052757 nitrogen Inorganic materials 0.000 claims description 65
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 58
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 51
• 125000001624 naphthyl group Chemical group 0.000 claims description 43
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 229920006395 saturated elastomer Polymers 0.000 claims description 24
• 125000004434 sulfur atom Chemical group 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
• UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000001425 triazolyl group Chemical group 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 125000005936 piperidyl group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000001769 aryl amino group Chemical group 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 1
• 229960000956 coumarin Drugs 0.000 claims 1
• 235000001671 coumarin Nutrition 0.000 claims 1
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
• 230000000845 anti-microbial effect Effects 0.000 abstract description 6
• 230000000843 anti-fungal effect Effects 0.000 abstract description 4
• 238000002360 preparation method Methods 0.000 abstract description 4
• 150000003839 salts Chemical class 0.000 abstract description 4
• 241001465754 Metazoa Species 0.000 abstract description 3
• 206010035660 Pneumocystis Infections Diseases 0.000 abstract description 3
• 206010073756 Pneumocystis jirovecii infection Diseases 0.000 abstract description 3
• 230000002401 inhibitory effect Effects 0.000 abstract description 3
• 208000035473 Communicable disease Diseases 0.000 abstract description 2
• 201000000317 pneumocystosis Diseases 0.000 abstract description 2
• 230000000069 prophylactic effect Effects 0.000 abstract description 2
• 230000001225 therapeutic effect Effects 0.000 abstract description 2
• 229920002498 Beta-glucan Polymers 0.000 abstract 1
• 208000005384 Pneumocystis Pneumonia Diseases 0.000 abstract 1
• 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 194
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 136
• 101150041968 CDC13 gene Proteins 0.000 description 134
• 238000000921 elemental analysis Methods 0.000 description 113
• 239000000203 mixture Substances 0.000 description 103
• 239000011734 sodium Substances 0.000 description 84
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 77
• 229910001868 water Inorganic materials 0.000 description 76
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 239000000243 solution Substances 0.000 description 71
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 70
• 229940093499 ethyl acetate Drugs 0.000 description 65
• 235000019439 ethyl acetate Nutrition 0.000 description 65
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 59
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 41
• 239000011541 reaction mixture Substances 0.000 description 41
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 35
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 239000000706 filtrate Substances 0.000 description 31
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
• 238000001914 filtration Methods 0.000 description 26
• 239000000725 suspension Substances 0.000 description 26
• 239000012964 benzotriazole Substances 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000002253 acid Substances 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• 238000004440 column chromatography Methods 0.000 description 23
• 239000002244 precipitate Substances 0.000 description 22
• BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 125000005447 octyloxy 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])O* 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• 229960001866 silicon dioxide Drugs 0.000 description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 15
• 229960000443 hydrochloric acid Drugs 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 239000007864 aqueous solution Substances 0.000 description 14
• 235000011167 hydrochloric acid Nutrition 0.000 description 14
• 125000004043 oxo group Chemical group O=* 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 13
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
• 229940050390 benzoate Drugs 0.000 description 10
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
• 125000005446 heptyloxy 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])O* 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 6
• UCGKVWNBKILEDM-UHFFFAOYSA-N C1=CC=C2[N+]([O-])=NNC2=C1 Chemical compound C1=CC=C2[N+]([O-])=NNC2=C1 UCGKVWNBKILEDM-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
• 229960004365 benzoic acid Drugs 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 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 6
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 229910052739 hydrogen Inorganic materials 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
• 235000010233 benzoic acid Nutrition 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 239000003456 ion exchange resin Substances 0.000 description 5
• 229920003303 ion-exchange polymer Polymers 0.000 description 5
• 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 5
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 239000001257 hydrogen Substances 0.000 description 4
• 238000001990 intravenous administration Methods 0.000 description 4
• 150000004702 methyl esters Chemical class 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
• PVRFWXFHUOIQLV-UHFFFAOYSA-N 1-amino-3-(4-octylphenyl)urea Chemical compound CCCCCCCCC1=CC=C(NC(=O)NN)C=C1 PVRFWXFHUOIQLV-UHFFFAOYSA-N 0.000 description 3
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
• PWGPANWHHZDAIP-UHFFFAOYSA-N 3-[4-(4-pentylphenyl)phenyl]propanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(CCC(O)=O)C=C1 PWGPANWHHZDAIP-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• 241000206607 Porphyra umbilicalis Species 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 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 3
• 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 description 3
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 238000000855 fermentation Methods 0.000 description 3
• 230000004151 fermentation Effects 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• 238000007918 intramuscular administration Methods 0.000 description 3
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
• 125000002757 morpholinyl group Chemical group 0.000 description 3
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• 239000011664 nicotinic acid Substances 0.000 description 3
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• KNFPLMFTXFVFPA-UHFFFAOYSA-N lithium;bis(2-methylpropyl)azanide Chemical compound CC(C)CN([Li])CC(C)C KNFPLMFTXFVFPA-UHFFFAOYSA-N 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 125000000628 margaroyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
• DHWRKYAZTBDRKA-VGOFMYFVSA-N methyl (E)-3-[4-(4-butoxyphenyl)phenyl]prop-2-enoate Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(\C=C\C(=O)OC)C=C1 DHWRKYAZTBDRKA-VGOFMYFVSA-N 0.000 description 1
• WZBUGBMBPXARJR-UHFFFAOYSA-N methyl 2-(4-hexoxyphenyl)-3h-benzimidazole-5-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC=C(C(=O)OC)C=C2N1 WZBUGBMBPXARJR-UHFFFAOYSA-N 0.000 description 1
• XKBMPKAAKSIFOR-UHFFFAOYSA-N methyl 2-[4-[4-[4-(5-methoxypentoxy)phenyl]phenyl]phenyl]acetate Chemical compound C1=CC(OCCCCCOC)=CC=C1C1=CC=C(C=2C=CC(CC(=O)OC)=CC=2)C=C1 XKBMPKAAKSIFOR-UHFFFAOYSA-N 0.000 description 1
• OQNUTBBRDVILAY-UHFFFAOYSA-N methyl 2-nonyl-3h-benzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2NC(CCCCCCCCC)=NC2=C1 OQNUTBBRDVILAY-UHFFFAOYSA-N 0.000 description 1
• DXHQGPCTERBXME-UHFFFAOYSA-N methyl 3-[4-(4-heptylphenyl)phenyl]prop-2-enoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C=CC(=O)OC)C=C1 DXHQGPCTERBXME-UHFFFAOYSA-N 0.000 description 1
• KSQITGOTJMYVHT-UHFFFAOYSA-N methyl 3-[4-(4-heptylphenyl)phenyl]propanoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 KSQITGOTJMYVHT-UHFFFAOYSA-N 0.000 description 1
• PKWJLGJNZNVUBD-UHFFFAOYSA-N methyl 3-[4-(4-pentoxyphenyl)phenyl]propanoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 PKWJLGJNZNVUBD-UHFFFAOYSA-N 0.000 description 1
• UIEPULRPIPFXGJ-UHFFFAOYSA-N methyl 3-[4-(4-pentylphenyl)phenyl]propanoate Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 UIEPULRPIPFXGJ-UHFFFAOYSA-N 0.000 description 1
• WWHGRCXLJLLWOX-UHFFFAOYSA-N methyl 4-(5-nonyl-1,3,4-oxadiazol-2-yl)benzoate Chemical compound O1C(CCCCCCCCC)=NN=C1C1=CC=C(C(=O)OC)C=C1 WWHGRCXLJLLWOX-UHFFFAOYSA-N 0.000 description 1
• OSEDFBIVKALVNN-UHFFFAOYSA-N methyl 4-(c-chloro-n-hydroxycarbonimidoyl)benzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=NO)C=C1 OSEDFBIVKALVNN-UHFFFAOYSA-N 0.000 description 1
• HGVBEQHEDXPHBI-UHFFFAOYSA-N methyl 4-(hydrazinecarbonyl)benzoate Chemical compound COC(=O)C1=CC=C(C(=O)NN)C=C1 HGVBEQHEDXPHBI-UHFFFAOYSA-N 0.000 description 1
• VVHXCSFDEMZQFY-UHFFFAOYSA-N methyl 4-(hydroxyiminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=NO)C=C1 VVHXCSFDEMZQFY-UHFFFAOYSA-N 0.000 description 1
• SVKDHMVSEYONNW-UHFFFAOYSA-N methyl 4-[3-(4-hexoxyphenyl)-1,2,4-oxadiazol-5-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(=O)OC)=N1 SVKDHMVSEYONNW-UHFFFAOYSA-N 0.000 description 1
• PAAXFOVYIVXHRP-UHFFFAOYSA-N methyl 4-[3-oxo-3-(4-pentoxyphenyl)prop-1-enyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)C=CC1=CC=C(C(=O)OC)C=C1 PAAXFOVYIVXHRP-UHFFFAOYSA-N 0.000 description 1
• MYSHSAIDZYLUKW-UHFFFAOYSA-N methyl 4-[3-oxo-3-(4-pentoxyphenyl)propanoyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)CC(=O)C1=CC=C(C(=O)OC)C=C1 MYSHSAIDZYLUKW-UHFFFAOYSA-N 0.000 description 1
• CIXYXCKHJMKPKG-UHFFFAOYSA-N methyl 4-[4-(8-oxo-8-piperidin-1-yloctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C=C1)=CC=C1OCCCCCCCC(=O)N1CCCCC1 CIXYXCKHJMKPKG-UHFFFAOYSA-N 0.000 description 1
• LVNCBSQQADVNFV-UHFFFAOYSA-N methyl 4-[5-(4-hexoxyphenyl)-1,3,4-thiadiazol-2-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(=O)OC)S1 LVNCBSQQADVNFV-UHFFFAOYSA-N 0.000 description 1
• JLCLOAYOQLRDSK-UHFFFAOYSA-N methyl 4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)OC)=NO1 JLCLOAYOQLRDSK-UHFFFAOYSA-N 0.000 description 1
• YNFQCAQISFKBES-UHFFFAOYSA-N methyl 4-[5-(4-piperidin-1-ylphenyl)-1,3,4-thiadiazol-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N2CCCCC2)S1 YNFQCAQISFKBES-UHFFFAOYSA-N 0.000 description 1
• WKFFUASNNKROGV-UHFFFAOYSA-N methyl 4-[[(4-cyclohexylbenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NNC(=O)C1=CC=C(C2CCCCC2)C=C1 WKFFUASNNKROGV-UHFFFAOYSA-N 0.000 description 1
• RWDNEZLUDJFINK-UHFFFAOYSA-N methyl 4-[[(4-octoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 RWDNEZLUDJFINK-UHFFFAOYSA-N 0.000 description 1
• YQYAPGKIASWFPE-UHFFFAOYSA-N methyl 4-[[(4-pentoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 YQYAPGKIASWFPE-UHFFFAOYSA-N 0.000 description 1
• CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
• IVYQLXCACCEQHM-UHFFFAOYSA-N methyl 4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C(=O)OC)C=C1 IVYQLXCACCEQHM-UHFFFAOYSA-N 0.000 description 1
• PJMMXLPXRYKMLD-UHFFFAOYSA-N methyl 5-[4-(4-butoxyphenyl)phenyl]furan-2-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C=2OC(=CC=2)C(=O)OC)C=C1 PJMMXLPXRYKMLD-UHFFFAOYSA-N 0.000 description 1
• MPUYLLIQJZUWBZ-UHFFFAOYSA-N methyl 6-(8-bromooctoxy)naphthalene-2-carboxylate Chemical compound C1=C(OCCCCCCCCBr)C=CC2=CC(C(=O)OC)=CC=C21 MPUYLLIQJZUWBZ-UHFFFAOYSA-N 0.000 description 1
• WPRSDVPSRCCIEQ-UHFFFAOYSA-N methyl 6-(8-methoxyoctoxy)naphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(OCCCCCCCCOC)=CC=C21 WPRSDVPSRCCIEQ-UHFFFAOYSA-N 0.000 description 1
• CGNQMJRSNZQYEW-UHFFFAOYSA-N methyl 6-[4-(4-heptoxyphenyl)piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OCCCCCCC)=CC=C1N1CCN(C=2N=CC(=CC=2)C(=O)OC)CC1 CGNQMJRSNZQYEW-UHFFFAOYSA-N 0.000 description 1
• PZDVVVLVCQRQSV-UHFFFAOYSA-N methyl 6-[4-[4-(8-bromooctoxy)phenyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1N1CCN(C=2C=CC(OCCCCCCCCBr)=CC=2)CC1 PZDVVVLVCQRQSV-UHFFFAOYSA-N 0.000 description 1
• MKSIUKCSAHIELM-UHFFFAOYSA-N methyl 6-heptylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(CCCCCCC)=CC=C21 MKSIUKCSAHIELM-UHFFFAOYSA-N 0.000 description 1
• OTGJDXGQXHXPLL-UHFFFAOYSA-N methyl 6-hex-1-ynylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C#CCCCC)=CC=C21 OTGJDXGQXHXPLL-UHFFFAOYSA-N 0.000 description 1
• HYWOJVCLXAQCPV-UHFFFAOYSA-N methyl 6-hexylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(CCCCCC)=CC=C21 HYWOJVCLXAQCPV-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• XPIHNCHVIZFNFJ-UHFFFAOYSA-N n'-hydroxy-4-octoxybenzenecarboximidamide Chemical compound CCCCCCCCOC1=CC=C(C(=N)NO)C=C1 XPIHNCHVIZFNFJ-UHFFFAOYSA-N 0.000 description 1
• UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
• VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 description 1
• 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
• AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
• CEMSSDOOIJDOBQ-UHFFFAOYSA-N phenyl n-(4-octylphenyl)carbamate Chemical compound C1=CC(CCCCCCCC)=CC=C1NC(=O)OC1=CC=CC=C1 CEMSSDOOIJDOBQ-UHFFFAOYSA-N 0.000 description 1
• XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
• CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
• 229960003424 phenylacetic acid Drugs 0.000 description 1
• 239000003279 phenylacetic acid Substances 0.000 description 1
• 125000001129 phenylbutoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 239000008363 phosphate buffer Substances 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• UXWKNNJFYZFNDI-UHFFFAOYSA-N piperazine;dihydrobromide Chemical compound Br.Br.C1CNCCN1 UXWKNNJFYZFNDI-UHFFFAOYSA-N 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
• IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 238000010298 pulverizing process Methods 0.000 description 1
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• 238000001226 reprecipitation Methods 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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• 230000000087 stabilizing effect Effects 0.000 description 1
• 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
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• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• YEHWSWXESXPBOS-UHFFFAOYSA-N tert-butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(O)C=C1 YEHWSWXESXPBOS-UHFFFAOYSA-N 0.000 description 1
• FIRYGSLIQPPZFE-UHFFFAOYSA-N tert-butyl 4-[4-(hydrazinecarbonylamino)phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(NC(=O)NN)C=C1 FIRYGSLIQPPZFE-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
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• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
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• 230000000699 topical effect Effects 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
• GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
• VVRBLMQPRNPMSX-UHFFFAOYSA-N trimethyl-[2-[4-(4-pentylphenyl)phenyl]ethynyl]silane Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#C[Si](C)(C)C)C=C1 VVRBLMQPRNPMSX-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
• 229920001567 vinyl ester resin Polymers 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1