KR100353303B1 - 항균활성을갖는고리형헥사펩티드 - Google Patents

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Publication number

KR100353303B1

KR100353303B1 KR1019970702213A KR19970702213A KR100353303B1 KR 100353303 B1 KR100353303 B1 KR 100353303B1 KR 1019970702213 A KR1019970702213 A KR 1019970702213A KR 19970702213 A KR19970702213 A KR 19970702213A KR 100353303 B1 KR100353303 B1 KR 100353303B1

Authority

KR

South Korea

Prior art keywords

alkoxy

phenyl

alkyl

substituted

alkanoyl

Prior art date

1994-10-07

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.)

Expired - Lifetime

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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 4
• 125000004122 cyclic group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 140
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 238000000034 method Methods 0.000 claims abstract description 25
• 229920001184 polypeptide Polymers 0.000 claims abstract description 22
• 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 22
• 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 22
• 208000015181 infectious disease Diseases 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 208000035473 Communicable disease Diseases 0.000 claims abstract description 4
• 241001465754 Metazoa Species 0.000 claims abstract description 4
• 238000011282 treatment Methods 0.000 claims abstract description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 464
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 263
• 125000000217 alkyl group Chemical group 0.000 claims description 258
• -1 Indolylcarbonyl Chemical group 0.000 claims description 191
• 125000001589 carboacyl group Chemical group 0.000 claims description 168
• 125000001424 substituent group Chemical group 0.000 claims description 136
• 125000000623 heterocyclic group Chemical group 0.000 claims description 105
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 69
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 125000001624 naphthyl group Chemical group 0.000 claims description 46
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 28
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 28
• 125000004434 sulfur atom Chemical group 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 17
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000004193 piperazinyl group Chemical group 0.000 claims description 13
• 125000005936 piperidyl group Chemical group 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 238000009423 ventilation Methods 0.000 claims description 5
• 241000228212 Aspergillus Species 0.000 claims description 4
• 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
• 241000186046 Actinomyces Species 0.000 claims description 2
• 241001480043 Arthrodermataceae Species 0.000 claims description 2
• 241001337994 Cryptococcus <scale insect> Species 0.000 claims description 2
• 241000233866 Fungi Species 0.000 claims description 2
• 241000223218 Fusarium Species 0.000 claims description 2
• 241000228402 Histoplasma Species 0.000 claims description 2
• 241000555676 Malassezia Species 0.000 claims description 2
• 241000235395 Mucor Species 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 230000037304 dermatophytes Effects 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 244000005700 microbiome Species 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• 244000000010 microbial pathogen Species 0.000 claims 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
• 125000000304 alkynyl 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
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
• 230000000392 somatic effect Effects 0.000 claims 1
• 230000000843 anti-fungal effect Effects 0.000 abstract description 4
• 230000002401 inhibitory effect Effects 0.000 abstract description 4
• 206010035664 Pneumonia Diseases 0.000 abstract description 3
• 229920002498 Beta-glucan Polymers 0.000 abstract description 2
• 238000011321 prophylaxis Methods 0.000 abstract 1
• 238000004519 manufacturing process Methods 0.000 description 379
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 204
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 172
• 125000003118 aryl group Chemical group 0.000 description 171
• 238000000921 elemental analysis Methods 0.000 description 119
• 239000000203 mixture Substances 0.000 description 108
• 230000002829 reductive effect Effects 0.000 description 91
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• 239000000243 solution Substances 0.000 description 87
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 86
• 235000019341 magnesium sulphate Nutrition 0.000 description 86
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
• 125000003435 aroyl group Chemical group 0.000 description 68
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 59
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
• 239000012044 organic layer Substances 0.000 description 50
• 239000011541 reaction mixture Substances 0.000 description 49
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
• 238000002360 preparation method Methods 0.000 description 43
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 239000012267 brine Substances 0.000 description 42
• 238000001914 filtration Methods 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 239000000706 filtrate Substances 0.000 description 37
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
• 239000003480 eluent Substances 0.000 description 29
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
• 239000000725 suspension Substances 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• 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 23
• 125000002950 monocyclic group Chemical group 0.000 description 21
• 206010057190 Respiratory tract infections Diseases 0.000 description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• 239000000741 silica gel Substances 0.000 description 17
• 229910002027 silica gel Inorganic materials 0.000 description 17
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 15
• 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 14
• 125000004043 oxo group Chemical group O=* 0.000 description 14
• 239000000843 powder Substances 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 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 10
• 125000004104 aryloxy group Chemical group 0.000 description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 8
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 8
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
• 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 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 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 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 239000000499 gel Substances 0.000 description 7
• 239000003456 ion exchange resin Substances 0.000 description 7
• 229920003303 ion-exchange polymer Polymers 0.000 description 7
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
• 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 6
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 5
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
• 125000001769 aryl amino group Chemical group 0.000 description 5
• 235000010233 benzoic acid Nutrition 0.000 description 5
• 239000012964 benzotriazole Substances 0.000 description 5
• 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 5
• 238000001704 evaporation Methods 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• 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 5
• 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 5
• 239000005457 ice water Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 125000005425 toluyl group Chemical group 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
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 239000000443 aerosol Substances 0.000 description 4
• 230000000845 anti-microbial effect Effects 0.000 description 4
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 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 4
• 125000002757 morpholinyl group Chemical group 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 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 4
• 125000001312 palmitoyl 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])[H] 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
• VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000008065 acid anhydrides Chemical class 0.000 description 3
• 125000005236 alkanoylamino group Chemical group 0.000 description 3
• 125000004171 alkoxy aryl group Chemical group 0.000 description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000006227 byproduct Substances 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 239000003054 catalyst Substances 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
• 238000005516 engineering process Methods 0.000 description 3
• 238000000855 fermentation Methods 0.000 description 3
• 230000004151 fermentation Effects 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
• DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 125000002632 imidazolidinyl group Chemical group 0.000 description 3
• 125000002883 imidazolyl group Chemical group 0.000 description 3
• 238000007918 intramuscular administration Methods 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
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• VRRBSYXFKWJTLW-UHFFFAOYSA-N methyl 3-[4-(4-pentylphenyl)phenyl]prop-2-enoate Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=CC(=O)OC)C=C1 VRRBSYXFKWJTLW-UHFFFAOYSA-N 0.000 description 3
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000003074 decanoyl 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(*)=O 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
• 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000003937 drug carrier Substances 0.000 description 1
• 229940112141 dry powder inhaler Drugs 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 150000002169 ethanolamines Chemical class 0.000 description 1
• GIZQNAYESPVBRM-UHFFFAOYSA-N ethyl 1-(6-heptoxynaphthalene-2-carbonyl)piperidine-4-carboxylate Chemical compound C1=CC2=CC(OCCCCCCC)=CC=C2C=C1C(=O)N1CCC(C(=O)OCC)CC1 GIZQNAYESPVBRM-UHFFFAOYSA-N 0.000 description 1
• ODQSOTBFWCNPKF-UHFFFAOYSA-N ethyl 2-(4-hexoxyphenyl)-1,3-benzoxazole-5-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC(C(=O)OCC)=CC=C2O1 ODQSOTBFWCNPKF-UHFFFAOYSA-N 0.000 description 1
• OSLQGOBYIDZZTD-UHFFFAOYSA-N ethyl 2-(6-octoxypyridin-3-yl)-1,3-benzoxazole-5-carboxylate Chemical compound C1=NC(OCCCCCCCC)=CC=C1C1=NC2=CC(C(=O)OCC)=CC=C2O1 OSLQGOBYIDZZTD-UHFFFAOYSA-N 0.000 description 1
• KILIQHMMEDQFJH-UHFFFAOYSA-N ethyl 2-[4-(4-hexylphenyl)phenyl]-1,3-benzoxazole-5-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2OC3=CC=C(C=C3N=2)C(=O)OCC)C=C1 KILIQHMMEDQFJH-UHFFFAOYSA-N 0.000 description 1
• RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
• UAHNKLUBOMFHKE-UHFFFAOYSA-N ethyl 4-[3-(4-pentoxyphenyl)prop-2-enoyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C=CC(=O)C1=CC=C(C(=O)OCC)C=C1 UAHNKLUBOMFHKE-UHFFFAOYSA-N 0.000 description 1
• PWLIDNJVLQJKIS-UHFFFAOYSA-N ethyl 4-[3-(dimethylamino)prop-2-enoyl]benzoate Chemical group CCOC(=O)C1=CC=C(C(=O)C=CN(C)C)C=C1 PWLIDNJVLQJKIS-UHFFFAOYSA-N 0.000 description 1
• WNJCQFLYGMSUJW-UHFFFAOYSA-N ethyl 4-[4-[1-(4-hexoxyphenyl)piperidin-4-yl]piperazin-1-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCC(N2CCN(CC2)C=2C=CC(=CC=2)C(=O)OCC)CC1 WNJCQFLYGMSUJW-UHFFFAOYSA-N 0.000 description 1
• GLOAPLPTWAXAIG-UHFFFAOYSA-N ethyl 4-acetylbenzoate Chemical compound CCOC(=O)C1=CC=C(C(C)=O)C=C1 GLOAPLPTWAXAIG-UHFFFAOYSA-N 0.000 description 1
• OQEHTFFLOHTFSB-UHFFFAOYSA-N ethyl 4-piperazin-1-ylbenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCNCC1 OQEHTFFLOHTFSB-UHFFFAOYSA-N 0.000 description 1
• IXJHHMIKLJPXMW-UHFFFAOYSA-N ethyl 6-[4-(4-hexoxyphenyl)piperazin-1-yl]pyridazine-3-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2N=NC(=CC=2)C(=O)OCC)CC1 IXJHHMIKLJPXMW-UHFFFAOYSA-N 0.000 description 1
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
• 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001072 heteroaryl group Chemical group 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 238000002329 infrared spectrum Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 125000000400 lauroyl 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])[H] 0.000 description 1
• KNFPLMFTXFVFPA-UHFFFAOYSA-N lithium;bis(2-methylpropyl)azanide Chemical compound CC(C)CN([Li])CC(C)C KNFPLMFTXFVFPA-UHFFFAOYSA-N 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• YZTQKMVBEGUONQ-UHFFFAOYSA-N manganese(4+) Chemical class [Mn+4] YZTQKMVBEGUONQ-UHFFFAOYSA-N 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
• 239000000463 material Substances 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
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• DFBUWLMRJBPCTJ-UHFFFAOYSA-N methyl 1-methyl-5-(4-octoxyphenyl)pyrazole-3-carboxylate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC(C(=O)OC)=NN1C DFBUWLMRJBPCTJ-UHFFFAOYSA-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
• 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
• VURTXDMCDUXUKM-UHFFFAOYSA-N methyl 3,4-dipentoxybenzoate Chemical compound CCCCCOC1=CC=C(C(=O)OC)C=C1OCCCCC VURTXDMCDUXUKM-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
• SSKROZKPITVKMK-UHFFFAOYSA-N methyl 4-(1-heptylpyrazol-4-yl)benzoate Chemical compound C1=NN(CCCCCCC)C=C1C1=CC=C(C(=O)OC)C=C1 SSKROZKPITVKMK-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
• WNYDFMUZTKXZNM-UHFFFAOYSA-N methyl 4-[(decanoylamino)carbamoyl]benzoate Chemical compound CCCCCCCCCC(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 WNYDFMUZTKXZNM-UHFFFAOYSA-N 0.000 description 1
• RJZGFGGJJGEFFT-UHFFFAOYSA-N methyl 4-[2-(4-hexoxyphenyl)pyrimidin-4-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC(C=2C=CC(=CC=2)C(=O)OC)=N1 RJZGFGGJJGEFFT-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
• DDWVXFQATJTOFS-UHFFFAOYSA-N methyl 4-[3-(4-hexoxyphenyl)-3-oxopropanoyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)CC(=O)C1=CC=C(C(=O)OC)C=C1 DDWVXFQATJTOFS-UHFFFAOYSA-N 0.000 description 1
• GMNUNXQGSOGPAT-UHFFFAOYSA-N methyl 4-[3-(4-pentoxyphenyl)-1,2-oxazol-5-yl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(=O)OC)=C1 GMNUNXQGSOGPAT-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
• ZOBQOLMFGUPNTI-UHFFFAOYSA-N methyl 4-[4-(8-bromooctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCCBr)C=C1 ZOBQOLMFGUPNTI-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
• DTJVUYGCIUXMOY-UHFFFAOYSA-N methyl 4-[5-(4-cyclohexylphenyl)-1,3,4-thiadiazol-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C2CCCCC2)S1 DTJVUYGCIUXMOY-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
• AGQJCMQLKCDQEL-UHFFFAOYSA-N methyl 4-[[(4-piperidin-1-ylbenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NNC(=O)C1=CC=C(N2CCCCC2)C=C1 AGQJCMQLKCDQEL-UHFFFAOYSA-N 0.000 description 1
• IKBJLIDFRQEDNL-UHFFFAOYSA-N methyl 4-[[[4-(4-propoxyphenyl)benzoyl]amino]carbamoyl]benzoate Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(=O)NNC(=O)C=2C=CC(=CC=2)C(=O)OC)C=C1 IKBJLIDFRQEDNL-UHFFFAOYSA-N 0.000 description 1
• INYNLXVGLZOULC-UHFFFAOYSA-N methyl 4-[[[4-(8-methoxyoctoxy)benzoyl]amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 INYNLXVGLZOULC-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
• 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
• OMKOCPWIXVQHHX-UHFFFAOYSA-N methyl 6-hept-1-ynylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C#CCCCCC)=CC=C21 OMKOCPWIXVQHHX-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
• 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
• UKZOPQRTQJERQC-UHFFFAOYSA-N methyl 6-hydroxynaphthalene-2-carboxylate Chemical compound C1=C(O)C=CC2=CC(C(=O)OC)=CC=C21 UKZOPQRTQJERQC-UHFFFAOYSA-N 0.000 description 1
• PXKNNGRTOQEZFY-UHFFFAOYSA-N methyl 7-octoxy-2-oxochromene-3-carboxylate Chemical compound C1=C(C(=O)OC)C(=O)OC2=CC(OCCCCCCCC)=CC=C21 PXKNNGRTOQEZFY-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 125000001419 myristoyl 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])[H] 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
• GUHXLVFLHWTLFJ-UHFFFAOYSA-N n'-hydroxy-4-octylbenzenecarboximidamide Chemical compound CCCCCCCCC1=CC=C(C(\N)=N\O)C=C1 GUHXLVFLHWTLFJ-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
• FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
• JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
• NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
• 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
• 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 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
• 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
• 125000001196 nonadecyl 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])C([H])([H])[H] 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
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