OA10475A - Cyclic hexapeptides having antibiotic activity - Google Patents

Cyclic hexapeptides having antibiotic activity Download PDF

Info

Publication number: OA10475A
Authority: OA; OAPI
Prior art keywords: alkoxy; phenyl; substituted; alkyl; hâve
Prior art date: 1994-10-07

Application number

OA60989A

Other languages

English (en)

Inventor

Hidenori Ohki

Masaki Tomishima

Akira Yamada

Hisashi Takasugi

Original Assignee

Fujisawa Pharmaceutical Co

Priority date (The priority date 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 date listed.)

1994-10-07

Filing date

1997-04-17

Publication date

2002-04-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26305774&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA10475(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-10-07 Priority claimed from GB9420425A external-priority patent/GB9420425D0/en

1995-04-28 Priority claimed from GBGB9508745.8A external-priority patent/GB9508745D0/en

1997-04-17 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

2002-04-08 Publication of OA10475A publication Critical patent/OA10475A/en

Links

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
235000001968 nicotinic acid Nutrition 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
125000002347 octyl 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])[H] 0.000 description 3
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 3
125000003373 pyrazinyl group Chemical group 0.000 description 3
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 3
125000003831 tetrazolyl group Chemical group 0.000 description 3
125000005425 toluyl group Chemical group 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ACFUNONLPCBJDR-UHFFFAOYSA-N 1-(4-hexoxyphenyl)piperidin-4-one Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCC(=O)CC1 ACFUNONLPCBJDR-UHFFFAOYSA-N 0.000 description 2
QHLVAKZJUURIQO-UHFFFAOYSA-N 1-(4-octoxyphenyl)piperazine Chemical compound C1=CC(OCCCCCCCC)=CC=C1N1CCNCC1 QHLVAKZJUURIQO-UHFFFAOYSA-N 0.000 description 2
RJQRJLCQHIMUQO-UHFFFAOYSA-N 1-bromo-4-(4-heptylphenyl)benzene Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(Br)C=C1 RJQRJLCQHIMUQO-UHFFFAOYSA-N 0.000 description 2
VXJTWTJULLKDPY-UHFFFAOYSA-N 1-bromo-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(Br)C=C1 VXJTWTJULLKDPY-UHFFFAOYSA-N 0.000 description 2
UXQBXLHGTWIYNR-UHFFFAOYSA-N 1-bromo-4-[4-(7-bromoheptoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCCBr)=CC=C1C1=CC=C(Br)C=C1 UXQBXLHGTWIYNR-UHFFFAOYSA-N 0.000 description 2
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
MKSWQHOPSDCVMS-UHFFFAOYSA-N 1-ethynyl-4-pentoxybenzene Chemical group CCCCCOC1=CC=C(C#C)C=C1 MKSWQHOPSDCVMS-UHFFFAOYSA-N 0.000 description 2
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ILWROKQKEDTIKB-UHFFFAOYSA-N 2-pentan-2-yloxy-1-phenylethanone Chemical compound CCCC(C)OCC(=O)C1=CC=CC=C1 ILWROKQKEDTIKB-UHFFFAOYSA-N 0.000 description 2
IEPCABVQANKPNT-UHFFFAOYSA-N 4-[4-(8-bromooctoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(OCCCCCCCCBr)C=C1 IEPCABVQANKPNT-UHFFFAOYSA-N 0.000 description 2
ZKSQOKZGDNEDJQ-UHFFFAOYSA-N 4-hexoxybenzohydrazide Chemical compound CCCCCCOC1=CC=C(C(=O)NN)C=C1 ZKSQOKZGDNEDJQ-UHFFFAOYSA-N 0.000 description 2
DQQOONVCLQZWOY-UHFFFAOYSA-N 4-hexoxybenzoyl chloride Chemical compound CCCCCCOC1=CC=C(C(Cl)=O)C=C1 DQQOONVCLQZWOY-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
WYAAQQHKARXGCD-UHFFFAOYSA-N 6-heptoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCCCCCCC)=CC=C21 WYAAQQHKARXGCD-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
KLQNJBAFEFFWQZ-UHFFFAOYSA-N benzoic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)C1=CC=CC=C1 KLQNJBAFEFFWQZ-UHFFFAOYSA-N 0.000 description 2
125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
AILAQOYFPLQIFN-UHFFFAOYSA-N butyl piperazine-1-carboxylate Chemical compound CCCCOC(=O)N1CCNCC1 AILAQOYFPLQIFN-UHFFFAOYSA-N 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 2
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
WQSOFWIIBNJWSS-UHFFFAOYSA-N ethyl 3-amino-4-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(N)=C1 WQSOFWIIBNJWSS-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000005956 isoquinolyl group Chemical group 0.000 description 2
125000001786 isothiazolyl group Chemical group 0.000 description 2
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 2
JZUXUPZONYEBIP-UHFFFAOYSA-N methyl 3-(6-heptoxynaphthalen-2-yl)propanoate Chemical compound C1=C(CCC(=O)OC)C=CC2=CC(OCCCCCCC)=CC=C21 JZUXUPZONYEBIP-UHFFFAOYSA-N 0.000 description 2
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 2
FUOKUWFZMCWRSJ-UHFFFAOYSA-N methyl 4-[4-(8-hydroxyoctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCCO)C=C1 FUOKUWFZMCWRSJ-UHFFFAOYSA-N 0.000 description 2
RUTXRPSNXSBXSF-UHFFFAOYSA-N methyl 4-[[(4-hexoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 RUTXRPSNXSBXSF-UHFFFAOYSA-N 0.000 description 2
FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 2
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 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 2
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
229940095574 propionic acid Drugs 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
125000005493 quinolyl group Chemical group 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
125000001984 thiazolidinyl group Chemical group 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
FKUPSFOZLYAVES-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(4-octoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N1CCN(C(=O)ON2C(CCC2=O)=O)CC1 FKUPSFOZLYAVES-UHFFFAOYSA-N 0.000 description 1
XICOPJZLUVZIGC-UHFFFAOYSA-N (2-nonyl-1,3-benzoxazol-5-yl)-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C1=CC=C(OC(CCCCCCCCC)=N2)C2=C1 XICOPJZLUVZIGC-UHFFFAOYSA-N 0.000 description 1
LKYTZJKPLMBBFO-UHFFFAOYSA-N (3-methyl-5-octyl-1-benzofuran-2-yl)-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C1=C(C)C2=CC(CCCCCCCC)=CC=C2O1 LKYTZJKPLMBBFO-UHFFFAOYSA-N 0.000 description 1
KMGPPFIECQFHKA-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[3-(4-pentoxyphenyl)-1,2-oxazol-5-yl]phenyl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)=C1 KMGPPFIECQFHKA-UHFFFAOYSA-N 0.000 description 1
KTLMRTLOUNMKIA-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[4-(4-pentoxyphenyl)piperazin-1-yl]phenyl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1N1CCN(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 KTLMRTLOUNMKIA-UHFFFAOYSA-N 0.000 description 1
VZEPZIRFHZJREF-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[4-(4-phenylcyclohexyl)piperazin-1-yl]phenyl]methanone Chemical compound C12=CC=CC=C2[N+]([O-])=NN1C(=O)C(C=C1)=CC=C1N(CC1)CCN1C(CC1)CCC1C1=CC=CC=C1 VZEPZIRFHZJREF-UHFFFAOYSA-N 0.000 description 1
YTDRFIFPDYISQX-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[4-[8-(tetrazol-2-yl)octoxy]phenyl]phenyl]methanone Chemical compound C12=CC=CC=C2[N+]([O-])=NN1C(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1OCCCCCCCCN1N=CN=N1 YTDRFIFPDYISQX-UHFFFAOYSA-N 0.000 description 1
VWXYRAGCRMWXHE-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]phenyl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)=NO1 VWXYRAGCRMWXHE-UHFFFAOYSA-N 0.000 description 1
NXIIMNFWIYYJIR-UHFFFAOYSA-N (3-oxidobenzotriazol-3-ium-1-yl)-[4-[5-[4-(4-propoxyphenyl)phenyl]-1,3,4-thiadiazol-2-yl]phenyl]methanone Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C=2SC(=NN=2)C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)C=C1 NXIIMNFWIYYJIR-UHFFFAOYSA-N 0.000 description 1
MMJKZWAJJWRULF-NMXAJACMSA-N (3s)-2-benzyl-3-hydroxy-1-(3-oxidobenzotriazol-3-ium-1-yl)hexadecan-1-one Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C([C@@H](O)CCCCCCCCCCCCC)CC1=CC=CC=C1 MMJKZWAJJWRULF-NMXAJACMSA-N 0.000 description 1
PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 1
VGRXAHXMIDCTNV-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)ON1C2=CC(Cl)=CC=C2N=N1 VGRXAHXMIDCTNV-UHFFFAOYSA-N 0.000 description 1
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
125000006532 (C3-C5) alkyl group Chemical group 0.000 description 1
CBWALJHXHCJYTE-HNNXBMFYSA-N (S)-3-hydroxypalmitic acid Chemical compound CCCCCCCCCCCCC[C@H](O)CC(O)=O CBWALJHXHCJYTE-HNNXBMFYSA-N 0.000 description 1
TUKVPSQRKJEBQQ-XDHOZWIPSA-N (e)-3-[4-(4-hex-5-enoxyphenyl)phenyl]-1-(3-oxidobenzotriazol-3-ium-1-yl)prop-2-en-1-one Chemical compound C12=CC=CC=C2[N+]([O-])=NN1C(=O)\C=C\C(C=C1)=CC=C1C1=CC=C(OCCCCC=C)C=C1 TUKVPSQRKJEBQQ-XDHOZWIPSA-N 0.000 description 1
KPKSOBGTNCWHCY-OVCLIPMQSA-N (e)-3-[4-[4-(6-methoxyhexoxy)phenyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(OCCCCCCOC)=CC=C1C1=CC=C(\C=C\C(O)=O)C=C1 KPKSOBGTNCWHCY-OVCLIPMQSA-N 0.000 description 1
CKOZACFGBXJVQB-CXUHLZMHSA-N (e)-3-[4-[4-(7-methoxyheptoxy)phenyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(OCCCCCCCOC)=CC=C1C1=CC=C(\C=C\C(O)=O)C=C1 CKOZACFGBXJVQB-CXUHLZMHSA-N 0.000 description 1
DHWXTSCSJKFYRT-KGENOOAVSA-N (e)-3-[4-[4-(8-methoxyoctoxy)phenyl]phenyl]-1-(3-oxidobenzotriazol-3-ium-1-yl)prop-2-en-1-one Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C(C=C1)=CC=C1\C=C\C(=O)N1C2=CC=CC=C2[N+]([O-])=N1 DHWXTSCSJKFYRT-KGENOOAVSA-N 0.000 description 1
XGHBOZVJLWVCCR-LICLKQGHSA-N (e)-3-[4-[4-(8-methoxyoctoxy)phenyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C1=CC=C(\C=C\C(O)=O)C=C1 XGHBOZVJLWVCCR-LICLKQGHSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
AGEIEHTVRJHTIV-UHFFFAOYSA-N 1-(3-oxidobenzotriazol-3-ium-1-yl)-3-[4-(4-pentoxyphenyl)phenyl]prop-2-en-1-one Chemical compound C1=CC(OCCCCC)=CC=C1C(C=C1)=CC=C1C=CC(=O)N1C2=CC=CC=C2[N+]([O-])=N1 AGEIEHTVRJHTIV-UHFFFAOYSA-N 0.000 description 1
OZWNMPULXAXAMJ-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)piperazine;dihydrobromide Chemical compound Br.Br.C1CCCCC1C1=CC=C(N2CCNCC2)C=C1 OZWNMPULXAXAMJ-UHFFFAOYSA-N 0.000 description 1
YJMZRISOAVIOBB-UHFFFAOYSA-N 1-(4-phenylcyclohexyl)piperazine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CNCCN1C1CCC(C=2C=CC=CC=2)CC1 YJMZRISOAVIOBB-UHFFFAOYSA-N 0.000 description 1
BGMOLNZRVXEEOF-UHFFFAOYSA-N 1-(6-heptoxynaphthalene-2-carbonyl)piperidine-4-carboxylic acid Chemical compound C1=CC2=CC(OCCCCCCC)=CC=C2C=C1C(=O)N1CCC(C(O)=O)CC1 BGMOLNZRVXEEOF-UHFFFAOYSA-N 0.000 description 1
QQQSUVSRXPLWAH-UHFFFAOYSA-N 1-[4-(4-heptylphenyl)phenyl]ethanone Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 QQQSUVSRXPLWAH-UHFFFAOYSA-N 0.000 description 1
UPLBTVYITAGXGL-UHFFFAOYSA-N 1-bromo-4-(4-butoxyphenyl)benzene Chemical group C1=CC(OCCCC)=CC=C1C1=CC=C(Br)C=C1 UPLBTVYITAGXGL-UHFFFAOYSA-N 0.000 description 1
KNNBCWVKTHEAKP-UHFFFAOYSA-N 1-bromo-4-[4-(6-bromohexoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCBr)=CC=C1C1=CC=C(Br)C=C1 KNNBCWVKTHEAKP-UHFFFAOYSA-N 0.000 description 1
VVQCBSVPEFWCGA-UHFFFAOYSA-N 1-bromo-4-[4-(6-fluorohexoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCF)=CC=C1C1=CC=C(Br)C=C1 VVQCBSVPEFWCGA-UHFFFAOYSA-N 0.000 description 1
NVVVHPJZHYYYLI-UHFFFAOYSA-N 1-bromo-4-[4-(7-fluoroheptoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCCF)=CC=C1C1=CC=C(Br)C=C1 NVVVHPJZHYYYLI-UHFFFAOYSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
SVHXPGWTCYKGGU-UHFFFAOYSA-N 1-ethynyl-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#C)C=C1 SVHXPGWTCYKGGU-UHFFFAOYSA-N 0.000 description 1
WQUQANRAAFHDNF-UHFFFAOYSA-N 1-heptyl-4-iodopyrazole Chemical compound CCCCCCCN1C=C(I)C=N1 WQUQANRAAFHDNF-UHFFFAOYSA-N 0.000 description 1
XCIFMWTYNQDDGV-UHFFFAOYSA-N 1-methyl-5-(4-octoxyphenyl)pyrazole-3-carboxylic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC(C(O)=O)=NN1C XCIFMWTYNQDDGV-UHFFFAOYSA-N 0.000 description 1
HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
IPXZUVMGAMNBTJ-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-1,3-benzoxazole-5-carboxylic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC(C(O)=O)=CC=C2O1 IPXZUVMGAMNBTJ-UHFFFAOYSA-N 0.000 description 1
FEPVDSQKTSBMKK-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2N1 FEPVDSQKTSBMKK-UHFFFAOYSA-N 0.000 description 1
SEIVGYPRRFSZOY-UHFFFAOYSA-N 2-(4-octoxyphenoxy)-1-(3-oxidobenzotriazol-3-ium-1-yl)propan-1-one Chemical compound C1=CC(OCCCCCCCC)=CC=C1OC(C)C(=O)N1C2=CC=CC=C2[N+]([O-])=N1 SEIVGYPRRFSZOY-UHFFFAOYSA-N 0.000 description 1
ZVNRMMKUQPXARN-UHFFFAOYSA-N 2-(4-octoxyphenoxy)acetic acid Chemical compound CCCCCCCCOC1=CC=C(OCC(O)=O)C=C1 ZVNRMMKUQPXARN-UHFFFAOYSA-N 0.000 description 1
CLGYXJLTRJDOEL-UHFFFAOYSA-N 2-(6-octoxypyridin-3-yl)-1,3-benzoxazole-5-carboxylic acid Chemical compound C1=NC(OCCCCCCCC)=CC=C1C1=NC2=CC(C(O)=O)=CC=C2O1 CLGYXJLTRJDOEL-UHFFFAOYSA-N 0.000 description 1
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
WKYPGMRZXGMVQA-UHFFFAOYSA-N 2-[4-(4-heptylphenyl)phenyl]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(=O)C(O)=O)C=C1 WKYPGMRZXGMVQA-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
AVZBOAGCVKEESJ-UHFFFAOYSA-O 2-ethyl-1,2-benzoxazol-2-ium-7-ol Chemical compound C1=CC(O)=C2O[N+](CC)=CC2=C1 AVZBOAGCVKEESJ-UHFFFAOYSA-O 0.000 description 1
BKUKXOMYGPYFJJ-UHFFFAOYSA-N 2-ethylsulfanyl-1h-benzimidazole;hydrobromide Chemical group Br.C1=CC=C2NC(SCC)=NC2=C1 BKUKXOMYGPYFJJ-UHFFFAOYSA-N 0.000 description 1
DQLXHSRVVQUSHR-UHFFFAOYSA-N 2-ethynyl-6-heptoxynaphthalene Chemical group C1=C(C#C)C=CC2=CC(OCCCCCCC)=CC=C21 DQLXHSRVVQUSHR-UHFFFAOYSA-N 0.000 description 1
SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
SBTKMQWDHADPNF-UHFFFAOYSA-N 2-methyl-2-(4-octoxyphenoxy)-1-(3-oxidobenzotriazol-3-ium-1-yl)propan-1-one Chemical compound C1=CC(OCCCCCCCC)=CC=C1OC(C)(C)C(=O)N1C2=CC=CC=C2[N+]([O-])=N1 SBTKMQWDHADPNF-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
KYDZGDHHKWMPKG-UHFFFAOYSA-N 2-nonyl-1,3-benzoxazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(CCCCCCCCC)=NC2=C1 KYDZGDHHKWMPKG-UHFFFAOYSA-N 0.000 description 1
GMBJQUCFSAGJNO-UHFFFAOYSA-N 2-nonyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(CCCCCCCCC)=NC2=C1 GMBJQUCFSAGJNO-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
PDMYKAFCDWAAID-UHFFFAOYSA-N 3,4-dipentoxybenzoic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=C1OCCCCC PDMYKAFCDWAAID-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
NSHAOELVDPKZIC-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonic acid;hydroxide Chemical compound [OH-].O1[N+](CC)=CC=C1C1=CC=CC(S(O)(=O)=O)=C1 NSHAOELVDPKZIC-UHFFFAOYSA-N 0.000 description 1
LWCDXXJJLFVTOG-UHFFFAOYSA-N 3-(4-pentoxyphenyl)prop-2-enal Chemical compound CCCCCOC1=CC=C(C=CC=O)C=C1 LWCDXXJJLFVTOG-UHFFFAOYSA-N 0.000 description 1
MTVOUNYCAWOPPQ-UHFFFAOYSA-N 3-(6-heptoxynaphthalen-2-yl)-1-(3-oxidobenzotriazol-3-ium-1-yl)prop-2-en-1-one Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C=CC1=CC2=CC=C(OCCCCCCC)C=C2C=C1 MTVOUNYCAWOPPQ-UHFFFAOYSA-N 0.000 description 1
HLVFZYSKMGVMJT-UHFFFAOYSA-N 3-(6-heptoxynaphthalen-2-yl)-1-(3-oxidobenzotriazol-3-ium-1-yl)propan-1-one Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)CCC1=CC2=CC=C(OCCCCCCC)C=C2C=C1 HLVFZYSKMGVMJT-UHFFFAOYSA-N 0.000 description 1
ZODPRHWKXOVAAN-UHFFFAOYSA-N 3-(6-heptoxynaphthalen-2-yl)prop-2-enoic acid Chemical compound C1=C(C=CC(O)=O)C=CC2=CC(OCCCCCCC)=CC=C21 ZODPRHWKXOVAAN-UHFFFAOYSA-N 0.000 description 1
GJFBPEQRLGLNJE-UHFFFAOYSA-N 3-(6-heptoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(CCC(O)=O)C=CC2=CC(OCCCCCCC)=CC=C21 GJFBPEQRLGLNJE-UHFFFAOYSA-N 0.000 description 1
HOKMTWJLJUSSLY-UHFFFAOYSA-N 3-[2-(4-hexylanilino)ethyl]-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.C1=CC(CCCCCC)=CC=C1NCCN1C(=O)OCC1 HOKMTWJLJUSSLY-UHFFFAOYSA-N 0.000 description 1
DQWCNYRPLHOZIY-UHFFFAOYSA-N 3-[4-(4-butoxyphenyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C=CC(O)=O)C=C1 DQWCNYRPLHOZIY-UHFFFAOYSA-N 0.000 description 1
WZAHDEUPYQZBGW-UHFFFAOYSA-N 3-[4-(4-heptylphenyl)phenyl]-1-(3-oxidobenzotriazol-3-ium-1-yl)prop-2-en-1-one Chemical compound C1=CC(CCCCCCC)=CC=C1C(C=C1)=CC=C1C=CC(=O)N1C2=CC=CC=C2[N+]([O-])=N1 WZAHDEUPYQZBGW-UHFFFAOYSA-N 0.000 description 1
OFUJQNIYHRBBFU-UHFFFAOYSA-N 3-[4-(4-heptylphenyl)phenyl]propanoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(CCC(O)=O)C=C1 OFUJQNIYHRBBFU-UHFFFAOYSA-N 0.000 description 1
NAULVRGGJFDILV-UHFFFAOYSA-N 3-[4-(4-pentoxyphenyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=CC(O)=O)C=C1 NAULVRGGJFDILV-UHFFFAOYSA-N 0.000 description 1
MWIWHZXYIFPWQF-UHFFFAOYSA-N 3-[4-(4-pentylphenyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=CC(O)=O)C=C1 MWIWHZXYIFPWQF-UHFFFAOYSA-N 0.000 description 1
BEUGGHYDMAZKJF-UHFFFAOYSA-N 3-[4-(4-pentylphenyl)phenyl]prop-2-ynoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C#CC(O)=O)C=C1 BEUGGHYDMAZKJF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NGTZFLWMWXTVOY-UHFFFAOYSA-N 3-fluoro-4-[4-(4-hexoxyphenyl)piperazin-1-yl]benzoic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCCCCCC)=CC=C1N1CCN(C=2C(=CC(=CC=2)C(O)=O)F)CC1 NGTZFLWMWXTVOY-UHFFFAOYSA-N 0.000 description 1
JPKKNTDFIUFNIX-UHFFFAOYSA-N 3-fluoro-4-[4-(4-hydroxyphenyl)piperazin-1-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1N1CCN(C=2C=CC(O)=CC=2)CC1 JPKKNTDFIUFNIX-UHFFFAOYSA-N 0.000 description 1
UHQJLSAZNHYLFW-UHFFFAOYSA-N 3-fluoro-4-[4-(4-methoxyphenyl)piperazin-1-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=CC(=CC=2)C#N)F)CC1 UHQJLSAZNHYLFW-UHFFFAOYSA-N 0.000 description 1
VBHYTUXWVBNUBL-UHFFFAOYSA-N 3-hydroxy-1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(=O)O)SC2=C1 VBHYTUXWVBNUBL-UHFFFAOYSA-N 0.000 description 1
NFHWJJPPGDLWQK-UHFFFAOYSA-N 3-methyl-5-octyl-1-benzofuran-2-carboxylic acid Chemical compound CCCCCCCCC1=CC=C2OC(C(O)=O)=C(C)C2=C1 NFHWJJPPGDLWQK-UHFFFAOYSA-N 0.000 description 1
XVROSBHWACAQRL-UHFFFAOYSA-N 4-(4-heptylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 XVROSBHWACAQRL-UHFFFAOYSA-N 0.000 description 1
USLZAESUXAJUQT-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzohydrazide Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(=O)NN)C=C1 USLZAESUXAJUQT-UHFFFAOYSA-N 0.000 description 1
IGIJSFNBEUBMGB-UHFFFAOYSA-N 4-(cyclohexyliminomethylideneamino)-n,n-diethylcyclohexan-1-amine Chemical compound C1CC(N(CC)CC)CCC1N=C=NC1CCCCC1 IGIJSFNBEUBMGB-UHFFFAOYSA-N 0.000 description 1
DJRKHTCUXRGYEU-UHFFFAOYSA-N 4-Hexyloxyaniline Chemical compound CCCCCCOC1=CC=C(N)C=C1 DJRKHTCUXRGYEU-UHFFFAOYSA-N 0.000 description 1
IGWVTENILPBXJK-UHFFFAOYSA-N 4-[3-(4-hexoxyphenyl)-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(O)=O)=N1 IGWVTENILPBXJK-UHFFFAOYSA-N 0.000 description 1
GKKDPUXAHZTMDA-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(C=2C=CC(O)=CC=2)CC1 GKKDPUXAHZTMDA-UHFFFAOYSA-N 0.000 description 1
YAYPIAMVDAPXIL-UHFFFAOYSA-N 4-[4-(4-octoxyphenyl)piperazin-1-yl]benzonitrile Chemical compound C1=CC(OCCCCCCCC)=CC=C1N1CCN(C=2C=CC(=CC=2)C#N)CC1 YAYPIAMVDAPXIL-UHFFFAOYSA-N 0.000 description 1
VLQVFMAPZWAKMW-UHFFFAOYSA-N 4-[4-(4-pentoxyphenyl)piperazin-1-yl]benzoic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCCCCC)=CC=C1N1CCN(C=2C=CC(=CC=2)C(O)=O)CC1 VLQVFMAPZWAKMW-UHFFFAOYSA-N 0.000 description 1
HTTUXJRISOCBEK-UHFFFAOYSA-N 4-[4-(5-phenoxypentoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C=C1)=CC=C1OCCCCCOC1=CC=CC=C1 HTTUXJRISOCBEK-UHFFFAOYSA-N 0.000 description 1
LXEIWYDDRKIJPV-UHFFFAOYSA-N 4-[4-(8-oxo-8-piperidin-1-yloctoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C=C1)=CC=C1OCCCCCCCC(=O)N1CCCCC1 LXEIWYDDRKIJPV-UHFFFAOYSA-N 0.000 description 1
ZTWQTRGPUZVOSC-UHFFFAOYSA-N 4-[4-[8-(2,6-dimethylmorpholin-4-yl)octoxy]phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1C(C)OC(C)CN1CCCCCCCCOC1=CC=C(C=2C=CC(=CC=2)C(O)=O)C=C1 ZTWQTRGPUZVOSC-UHFFFAOYSA-N 0.000 description 1
FYBZFCKWGXJFKK-UHFFFAOYSA-N 4-[5-(4-cyclohexylphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C2CCCCC2)S1 FYBZFCKWGXJFKK-UHFFFAOYSA-N 0.000 description 1
XFPBZYIDFWFBOA-UHFFFAOYSA-N 4-[5-(4-hexoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(O)=O)O1 XFPBZYIDFWFBOA-UHFFFAOYSA-N 0.000 description 1
PIAVEPBCWWSSAY-UHFFFAOYSA-N 4-[5-(4-hexoxyphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(O)=O)S1 PIAVEPBCWWSSAY-UHFFFAOYSA-N 0.000 description 1
JJYMAZPWFNSWSF-UHFFFAOYSA-N 4-[5-(4-octoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(O)=O)O1 JJYMAZPWFNSWSF-UHFFFAOYSA-N 0.000 description 1
UGHHSCGTCCBZGA-UHFFFAOYSA-N 4-[5-(4-octoxyphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(O)=O)S1 UGHHSCGTCCBZGA-UHFFFAOYSA-N 0.000 description 1
PDTXSIGPZDVVIX-UHFFFAOYSA-N 4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoic acid Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(O)=O)=NO1 PDTXSIGPZDVVIX-UHFFFAOYSA-N 0.000 description 1
UXBMCTOADKRHBZ-UHFFFAOYSA-N 4-[5-[4-(4-propoxyphenyl)phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C=2SC(=NN=2)C=2C=CC(=CC=2)C(O)=O)C=C1 UXBMCTOADKRHBZ-UHFFFAOYSA-N 0.000 description 1
SFMJCBKNKOWTOT-UHFFFAOYSA-N 4-[5-[4-(8-methoxyoctoxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(O)=O)S1 SFMJCBKNKOWTOT-UHFFFAOYSA-N 0.000 description 1
HXNXLXRDDTYQTG-UHFFFAOYSA-N 4-cyclohexylbenzohydrazide Chemical compound C1=CC(C(=O)NN)=CC=C1C1CCCCC1 HXNXLXRDDTYQTG-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 1
FQNPEJUAXSAVMQ-UHFFFAOYSA-N 4-hexoxy-n'-hydroxybenzenecarboximidamide Chemical compound CCCCCCOC1=CC=C(C(N)=NO)C=C1 FQNPEJUAXSAVMQ-UHFFFAOYSA-N 0.000 description 1
GWXUVWKBVROFDM-UHFFFAOYSA-N 4-hexoxybenzaldehyde Chemical compound CCCCCCOC1=CC=C(C=O)C=C1 GWXUVWKBVROFDM-UHFFFAOYSA-N 0.000 description 1
ZBOKEVFJYLXVJQ-UHFFFAOYSA-N 4-hexoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CCCCCCOC1=CC=C(C(N)=N)C=C1 ZBOKEVFJYLXVJQ-UHFFFAOYSA-N 0.000 description 1
HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 1
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 1
HFRUPPHPJRZOCM-UHFFFAOYSA-N 4-octoxyphenol Chemical compound CCCCCCCCOC1=CC=C(O)C=C1 HFRUPPHPJRZOCM-UHFFFAOYSA-N 0.000 description 1
ORKQJTBYQZITLA-UHFFFAOYSA-N 4-octylaniline Chemical compound CCCCCCCCC1=CC=C(N)C=C1 ORKQJTBYQZITLA-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
YAPVGSXODFOBBR-UHFFFAOYSA-N 4-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1 YAPVGSXODFOBBR-UHFFFAOYSA-N 0.000 description 1
NLDYZVXJDDWPJI-UHFFFAOYSA-N 4-piperidin-1-ylbenzohydrazide Chemical compound C1=CC(C(=O)NN)=CC=C1N1CCCCC1 NLDYZVXJDDWPJI-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
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 description 1
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
BJIXCPRZEQZYTC-UHFFFAOYSA-N 5-(4-octoxyphenyl)-1,2-oxazole-3-carboxylic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC(C(O)=O)=NO1 BJIXCPRZEQZYTC-UHFFFAOYSA-N 0.000 description 1
PNWUVMQJFCWBOY-UHFFFAOYSA-N 5-[4-(4-butoxyphenyl)phenyl]furan-2-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C=2OC(=CC=2)C(O)=O)C=C1 PNWUVMQJFCWBOY-UHFFFAOYSA-N 0.000 description 1
MGNMPIQWBOVLFX-UHFFFAOYSA-N 5-methoxy-1-benzothiophene-2-carboxamide Chemical compound COC1=CC=C2SC(C(N)=O)=CC2=C1 MGNMPIQWBOVLFX-UHFFFAOYSA-N 0.000 description 1
TZVWFVNRJGQBDZ-UHFFFAOYSA-N 5-octoxy-1-benzothiophene-2-carboxylic acid Chemical compound CCCCCCCCOC1=CC=C2SC(C(O)=O)=CC2=C1 TZVWFVNRJGQBDZ-UHFFFAOYSA-N 0.000 description 1
BECWGGXKSFAUNK-UHFFFAOYSA-N 6-(4-heptoxyphenyl)pyridine-3-carboxylic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=N1 BECWGGXKSFAUNK-UHFFFAOYSA-N 0.000 description 1
YKGKZQHPSPKBRS-UHFFFAOYSA-N 6-(8-methoxyoctoxy)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCCCCCCCCOC)=CC=C21 YKGKZQHPSPKBRS-UHFFFAOYSA-N 0.000 description 1
QHKRRELVDJFOEK-UHFFFAOYSA-N 6-(octoxymethyl)pyridine-2-carboxylic acid Chemical compound CCCCCCCCOCC1=CC=CC(C(O)=O)=N1 QHKRRELVDJFOEK-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
UJLHMYSJHQTVGT-UHFFFAOYSA-N 6-[4-(4-heptoxyphenyl)piperazin-1-yl]pyridine-3-carboxylic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1N1CCN(C=2N=CC(=CC=2)C(O)=O)CC1 UJLHMYSJHQTVGT-UHFFFAOYSA-N 0.000 description 1
YPZQQHKCPCCPJB-UHFFFAOYSA-N 6-[4-(4-hexoxyphenyl)piperazin-1-yl]pyridazine-3-carboxylic acid Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2N=NC(=CC=2)C(O)=O)CC1 YPZQQHKCPCCPJB-UHFFFAOYSA-N 0.000 description 1
NODUXQYADMUDML-UHFFFAOYSA-N 6-[4-[4-(8-methoxyoctoxy)phenyl]piperazin-1-yl]pyridine-3-carboxylic acid Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1N1CCN(C=2N=CC(=CC=2)C(O)=O)CC1 NODUXQYADMUDML-UHFFFAOYSA-N 0.000 description 1
UWYDUSKEEPMFNU-UHFFFAOYSA-N 6-heptoxynaphthalene-2-carbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(OCCCCCCC)=CC=C21 UWYDUSKEEPMFNU-UHFFFAOYSA-N 0.000 description 1
OURHICMQMQBYDD-UHFFFAOYSA-N 6-heptylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(CCCCCCC)=CC=C21 OURHICMQMQBYDD-UHFFFAOYSA-N 0.000 description 1
ZJJWBEVVSDIYCS-UHFFFAOYSA-N 6-hexylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(CCCCCC)=CC=C21 ZJJWBEVVSDIYCS-UHFFFAOYSA-N 0.000 description 1
HIKCRLDSCSWXML-UHFFFAOYSA-N 7-hydroxy-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate Chemical compound C1=C(O)C=C2CNC(C(=O)O)CC2=C1 HIKCRLDSCSWXML-UHFFFAOYSA-N 0.000 description 1
APKYVNBTBYUCAR-UHFFFAOYSA-N 7-octoxy-2-oxochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)OC2=CC(OCCCCCCCC)=CC=C21 APKYVNBTBYUCAR-UHFFFAOYSA-N 0.000 description 1
XHSGKIGWAVPNES-UHFFFAOYSA-N 7-octoxy-3-(3-oxidobenzotriazol-3-ium-1-carbonyl)chromen-2-one Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C1=CC2=CC=C(OCCCCCCCC)C=C2OC1=O XHSGKIGWAVPNES-UHFFFAOYSA-N 0.000 description 1
241000186046 Actinomyces Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
QVDADLDKQLWJRR-OVCLIPMQSA-N C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCC(C)C)C=C1 Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCC(C)C)C=C1 QVDADLDKQLWJRR-OVCLIPMQSA-N 0.000 description 1
FOQWICUNDZMIOR-CXUHLZMHSA-N C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCF)C=C1 Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCF)C=C1 FOQWICUNDZMIOR-CXUHLZMHSA-N 0.000 description 1
JCMQZYHTGVPSGY-OVCLIPMQSA-N C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCCCCF)C=C1 Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1C1=CC=C(OCCCCCCF)C=C1 JCMQZYHTGVPSGY-OVCLIPMQSA-N 0.000 description 1
QPQOLNDKAGSNJG-WKILWMFISA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 QPQOLNDKAGSNJG-WKILWMFISA-N 0.000 description 1
MBWRHUSKMKZTLJ-XYPYZODXSA-N CCCCC[C@H]1CC[C@H](C(=O)NN)CC1 Chemical compound CCCCC[C@H]1CC[C@H](C(=O)NN)CC1 MBWRHUSKMKZTLJ-XYPYZODXSA-N 0.000 description 1
HGUTZFSEOVENGN-UHFFFAOYSA-N COC(C1=CC=C(C=NO)C=C1)=O.Cl Chemical compound COC(C1=CC=C(C=NO)C=C1)=O.Cl HGUTZFSEOVENGN-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001158911 Coleophoma sp. Species 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
229920001503 Glucan Polymers 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
241000228402 Histoplasma Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241000555676 Malassezia Species 0.000 description 1
WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
241000235395 Mucor Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
PHCBEOGBQHYFOQ-UHFFFAOYSA-N ON=CC(C=C1)=CC=C1Br.Cl Chemical compound ON=CC(C=C1)=CC=C1Br.Cl PHCBEOGBQHYFOQ-UHFFFAOYSA-N 0.000 description 1
LTVJUWMNVJQUHP-IBGZPJMESA-N O[C@H](CC(=O)N1N=NC2=C1C=CC=C2)CCCCCCCCCCCCC Chemical compound O[C@H](CC(=O)N1N=NC2=C1C=CC=C2)CCCCCCCCCCCCC LTVJUWMNVJQUHP-IBGZPJMESA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000233870 Pneumocystis Species 0.000 description 1
241000233872 Pneumocystis carinii Species 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
NUOITAPZZREUHB-ZZTVPSNHSA-N [(16R)-1-methoxy-18-(3-oxidobenzotriazol-3-ium-1-yl)-18-oxo-16-phenylmethoxyoctadecyl]carbamic acid Chemical compound C(C1=CC=CC=C1)O[C@@H](CC(=O)N1N=[N+](C2=C1C=CC=C2)[O-])CCCCCCCCCCCCCCC(OC)NC(=O)O NUOITAPZZREUHB-ZZTVPSNHSA-N 0.000 description 1
RCDVMGKQZXRFFS-UHFFFAOYSA-N [2-(4-hexoxyphenyl)-1,3-benzoxazol-5-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC(C(=O)N3C4=CC=CC=C4[N+]([O-])=N3)=CC=C2O1 RCDVMGKQZXRFFS-UHFFFAOYSA-N 0.000 description 1
YBUQLLNWXLFPFG-UHFFFAOYSA-N [2-(6-octoxypyridin-3-yl)-1,3-benzoxazol-5-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=NC(OCCCCCCCC)=CC=C1C1=NC2=CC(C(=O)N3C4=CC=CC=C4[N+]([O-])=N3)=CC=C2O1 YBUQLLNWXLFPFG-UHFFFAOYSA-N 0.000 description 1
USZQQNCSTSTRGY-UHFFFAOYSA-N [2-[4-(4-hexylphenyl)phenyl]-1,3-benzoxazol-5-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2OC3=CC=C(C=C3N=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)C=C1 USZQQNCSTSTRGY-UHFFFAOYSA-N 0.000 description 1
CJSGOXIDHWGIRY-UHFFFAOYSA-N [3-[(6-heptoxynaphthalen-2-yl)methyl]-2,5-dioxopyrrolidin-1-yl] hydrogen carbonate Chemical compound C1=CC2=CC(OCCCCCCC)=CC=C2C=C1CC1CC(=O)N(OC(O)=O)C1=O CJSGOXIDHWGIRY-UHFFFAOYSA-N 0.000 description 1
YLNHWXROHCEXCT-UHFFFAOYSA-N [3-chloro-4-[4-(4-hexoxyphenyl)piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2C(=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)Cl)CC1 YLNHWXROHCEXCT-UHFFFAOYSA-N 0.000 description 1
DNMZOWZAWNQRSO-UHFFFAOYSA-N [3-fluoro-4-[4-(4-hexoxyphenyl)piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2C(=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)F)CC1 DNMZOWZAWNQRSO-UHFFFAOYSA-N 0.000 description 1
FLHSCSJTCSAHDJ-UHFFFAOYSA-N [4-(4-butoxyphenyl)phenyl]boronic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(B(O)O)C=C1 FLHSCSJTCSAHDJ-UHFFFAOYSA-N 0.000 description 1
MWEWQDMVKHCOSZ-UHFFFAOYSA-N [4-(4-heptylphenyl)phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)C=C1 MWEWQDMVKHCOSZ-UHFFFAOYSA-N 0.000 description 1
FQYALAYSGVPARL-UHFFFAOYSA-N [4-[2-(4-hexoxyphenyl)pyrimidin-4-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)=N1 FQYALAYSGVPARL-UHFFFAOYSA-N 0.000 description 1
TYFGTWVTKJCORA-UHFFFAOYSA-N [4-[3-(4-hexoxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)=N1 TYFGTWVTKJCORA-UHFFFAOYSA-N 0.000 description 1
KMYVCLSBRKRFFJ-UHFFFAOYSA-N [4-[4-(4-hexoxyphenyl)piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 KMYVCLSBRKRFFJ-UHFFFAOYSA-N 0.000 description 1
KNOZJVIQPCEWFO-UHFFFAOYSA-N [4-[4-(4-hexylphenyl)piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(CCCCCC)=CC=C1N1CCN(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 KNOZJVIQPCEWFO-UHFFFAOYSA-N 0.000 description 1
OCBVZLAURCOAHB-UHFFFAOYSA-N [4-[4-(5-methoxypentoxy)phenyl]phenyl]boronic acid Chemical compound C1=CC(OCCCCCOC)=CC=C1C1=CC=C(B(O)O)C=C1 OCBVZLAURCOAHB-UHFFFAOYSA-N 0.000 description 1
AGQJYXDYYXKDRV-UHFFFAOYSA-N [4-[4-(6-methoxyhexoxy)phenyl]phenyl]boronic acid Chemical compound C1=CC(OCCCCCCOC)=CC=C1C1=CC=C(B(O)O)C=C1 AGQJYXDYYXKDRV-UHFFFAOYSA-N 0.000 description 1
RWXCUZKLRMKKNH-UHFFFAOYSA-N [4-[4-[1-(4-hexoxyphenyl)piperidin-4-yl]piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCC(N2CCN(CC2)C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 RWXCUZKLRMKKNH-UHFFFAOYSA-N 0.000 description 1
WNRGGOKCTNJGMY-UHFFFAOYSA-N [4-[4-[4-(6-methoxyhexoxy)phenyl]phenyl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCCOC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)C=C1 WNRGGOKCTNJGMY-UHFFFAOYSA-N 0.000 description 1
WAJQDVTYMMCAKT-UHFFFAOYSA-N [4-[4-[4-(8-methoxyoctoxy)phenyl]piperazin-1-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1N1CCN(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 WAJQDVTYMMCAKT-UHFFFAOYSA-N 0.000 description 1
NSDRWIFMUWNFAY-UHFFFAOYSA-N [4-[5-(4-octoxyphenyl)-1,3,4-thiadiazol-2-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)S1 NSDRWIFMUWNFAY-UHFFFAOYSA-N 0.000 description 1
VAUUUITVJADHRZ-UHFFFAOYSA-N [4-[5-[4-(8-methoxyoctoxy)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)O1 VAUUUITVJADHRZ-UHFFFAOYSA-N 0.000 description 1
XVLAYOKCKRVSOO-UHFFFAOYSA-N [6-(8-methoxyoctoxy)naphthalen-2-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)C1=CC2=CC=C(OCCCCCCCCOC)C=C2C=C1 XVLAYOKCKRVSOO-UHFFFAOYSA-N 0.000 description 1
LYRDPUZGBKFDCP-UHFFFAOYSA-N [6-(octoxymethyl)pyridin-2-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound CCCCCCCCOCC1=CC=CC(C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)=N1 LYRDPUZGBKFDCP-UHFFFAOYSA-N 0.000 description 1
XCVALDRAFAUOEH-UHFFFAOYSA-N [6-[4-(4-butoxyphenyl)phenyl]pyridin-3-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C=2N=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)C=C1 XCVALDRAFAUOEH-UHFFFAOYSA-N 0.000 description 1
FPEFYXKNLVHVBY-UHFFFAOYSA-N [6-[4-(4-heptoxyphenyl)piperazin-1-yl]pyridin-3-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCCC)=CC=C1N1CCN(C=2N=CC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 FPEFYXKNLVHVBY-UHFFFAOYSA-N 0.000 description 1
GANBDWTWKJHOPG-UHFFFAOYSA-N [6-[4-(4-hexoxyphenyl)piperazin-1-yl]pyridazin-3-yl]-(3-oxidobenzotriazol-3-ium-1-yl)methanone Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2N=NC(=CC=2)C(=O)N2C3=CC=CC=C3[N+]([O-])=N2)CC1 GANBDWTWKJHOPG-UHFFFAOYSA-N 0.000 description 1
XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
125000001124 arachidoyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
YFWQNQKGKBBXIP-UHFFFAOYSA-N benzotriazol-1-yl-(3,4-dipentoxyphenyl)methanone Chemical compound C1=C(OCCCCC)C(OCCCCC)=CC=C1C(=O)N1C2=CC=CC=C2N=N1 YFWQNQKGKBBXIP-UHFFFAOYSA-N 0.000 description 1
CUVWPIXYWHSJIX-UHFFFAOYSA-N benzotriazol-1-yl-(6-heptylnaphthalen-2-yl)methanone Chemical compound N1=NC2=CC=CC=C2N1C(=O)C1=CC2=CC=C(CCCCCCC)C=C2C=C1 CUVWPIXYWHSJIX-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[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
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 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
238000003113 dilution method Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
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
239000008298 dragée Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
CAMDZZUCCKSMPS-FMQUCBEESA-N ethyl (e)-3-[4-(4-heptylphenyl)phenyl]but-2-enoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(\C)=C\C(=O)OCC)C=C1 CAMDZZUCCKSMPS-FMQUCBEESA-N 0.000 description 1
RILLRPWNMMZZBV-UHFFFAOYSA-N ethyl 1-(4-hexoxyphenyl)-4-oxopiperidine-3-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CC(C(=O)OCC)C(=O)CC1 RILLRPWNMMZZBV-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
XHMVKIOQESEIKX-UHFFFAOYSA-N ethyl 3-methyl-5-octyl-1-benzofuran-2-carboxylate Chemical compound CCCCCCCCC1=CC=C2OC(C(=O)OCC)=C(C)C2=C1 XHMVKIOQESEIKX-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
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
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
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000001041 indolyl group Chemical group 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
238000005342 ion exchange Methods 0.000 description 1
238000001871 ion mobility spectroscopy Methods 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 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
210000004072 lung Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
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
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
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
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
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
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
230000008719 thickening Effects 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Epidemiology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

OA60989A 1994-10-07 1997-04-17 Cyclic hexapeptides having antibiotic activity OA10475A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9420425A GB9420425D0 (en)	1994-10-07	1994-10-07	New compound
GBGB9508745.8A GB9508745D0 (en)	1995-04-28	1995-04-28	New compound

Publications (1)

Publication Number	Publication Date
OA10475A true OA10475A (en)	2002-04-08

Family

ID=26305774

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60989A OA10475A (en)	1994-10-07	1997-04-17	Cyclic hexapeptides having antibiotic activity

Country Status (26)

Country	Link
US (2)	US6107458A (fr)
EP (1)	EP0788511B1 (fr)
JP (2)	JP2897427B2 (fr)
KR (1)	KR100353303B1 (fr)
CN (1)	CN1203089C (fr)
AR (1)	AR041770A1 (fr)
AT (1)	ATE229541T1 (fr)
AU (1)	AU696949B2 (fr)
BR (2)	BR9504791B1 (fr)
CA (1)	CA2202058C (fr)
DE (2)	DE122008000025I2 (fr)
DK (1)	DK0788511T3 (fr)
ES (1)	ES2187575T3 (fr)
FI (1)	FI119988B (fr)
FR (1)	FR08C0028I2 (fr)
HU (1)	HU228151B1 (fr)
IL (1)	IL115484A (fr)
LU (1)	LU91452I2 (fr)
MX (1)	MX9702531A (fr)
NL (1)	NL300352I2 (fr)
NO (2)	NO328483B1 (fr)
OA (1)	OA10475A (fr)
PT (1)	PT788511E (fr)
RU (1)	RU2165423C2 (fr)
TR (1)	TR199501229A2 (fr)
WO (1)	WO1996011210A1 (fr)

Families Citing this family (61)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5696084A (en) *	1996-08-16	1997-12-09	Abbott Laboratories	Amino-lipopetide antifungal agents
AUPO371596A0 (en) *	1996-11-19	1996-12-12	Fujisawa Pharmaceutical Co., Ltd.	New compound
AUPO381496A0 (en) *	1996-11-25	1996-12-19	Fujisawa Pharmaceutical Co., Ltd.	New compound
US6291680B1 (en) *	1997-06-18	2001-09-18	Fujisawa Pharmaceutical Co., Ltd.	Production process
HUP0102515A3 (en) *	1998-02-09	2001-12-28	Fujisawa Pharmaceutical Co	Cyclopeptides, process for their preparation, pharmaceutical compositions comprising thereof and their use
AU756792B2 (en) *	1998-02-09	2003-01-23	Fujisawa Pharmaceutical Co., Ltd.	New compound
US7084279B1 (en) *	1999-02-11	2006-08-01	Emisphere Technologies Inc.	Oxadiazole compounds and compositions for delivering active agents
WO2000047188A1 (fr) *	1999-02-11	2000-08-17	Emisphere Technologies, Inc.	Composes a base d'oxadiazole et compositions destinees a l'apport d'agents actifs
AUPP999799A0 (en)	1999-04-27	1999-05-20	Fujisawa Pharmaceutical Co., Ltd.	New compound
AUPQ066399A0 (en) *	1999-05-31	1999-06-24	Fujisawa Pharmaceutical Co., Ltd.	Antifungal combination use
TWI233805B (en) *	1999-07-01	2005-06-11	Fujisawa Pharmaceutical Co	Stabilized pharmaceutical composition in lyophilized form as antifungal agent
AU6564000A (en) *	1999-07-27	2001-02-13	Aventis Pharma Deutschland Gmbh	Novel cyclohexapeptide compounds, processes for their production and their use as a pharmaceutical
AUPQ462399A0 (en) *	1999-12-13	2000-01-13	Fujisawa Pharmaceutical Co., Ltd.	New use
TWI250992B (en)	2000-02-21	2006-03-11	Astellas Pharma Inc	Polypeptide compounds for the prophylactic and/or therapeutic treatment of infectious diseases caused by pathogenic microorganisms
ES2191516B1 (es) *	2000-07-28	2005-01-01	Consejo Superior De Investigaciones Cientificas	Antibioticos antifungicos de naturaleza peptidica inhibidores de la germinacion y el crecimiento de hongos fitopatogenos.
AUPQ938700A0 (en) *	2000-08-14	2000-09-07	Fujisawa Pharmaceutical Co., Ltd.	Antifungal combination use
DE60234812D1 (de)	2001-01-29	2010-02-04	Shionogi & Co	Arzneipräparat, das als wirkstoff 5-methyl-1-phenyl-2-(1h)-pyridon enthält
JP2005053782A (ja) *	2001-08-31	2005-03-03	Fujisawa Pharmaceut Co Ltd	環状リポペプチド化合物の新規結晶
IL163666A0 (en)	2002-02-22	2005-12-18	New River Pharmaceuticals Inc	Active agent delivery systems and methods for protecting and administering active agents
JP4784093B2 (ja) *	2002-08-08	2011-09-28	アステラス製薬株式会社	イソオキサゾリル安息香酸の製造法
AU2003903205A0 (en) *	2003-06-23	2003-07-10	Fujisawa Pharmaceutical Co., Ltd.	New compound
EP1654036B1 (fr) *	2003-07-22	2007-12-26	Theravance, Inc.	Utilisation d'un agent antifongique a base d'echinocandines conjointement avec un agent antibacterien glycopeptidique
WO2005026323A2 (fr) *	2003-09-05	2005-03-24	Merck & Co., Inc.	Phases stationnaires et procede de purification mettant en oeuvre lesdites phases
WO2005028438A1 (fr) *	2003-09-22	2005-03-31	Banyu Pharmaceutical Co., Ltd.	Nouveau derive de piperidine
US7476673B2 (en) *	2003-12-30	2009-01-13	Allergan, Inc.	Disubstituted chalcone oximes as selective agonists of RARγ retinoid receptors
AU2005245470A1 (en) *	2004-05-20	2005-12-01	Foldrx Pharmaceuticals, Inc.	2-((hetero) aryl)-benzoxazole compounds and derivatives, compositions and methods for stabilizing transthyretin and inhibiting transthyretin misfolding
TW200626138A (en)	2004-09-20	2006-08-01	Xenon Pharmaceuticals Inc	Heterocyclic derivatives and their use as therapeutic agents
AR051026A1 (es)	2004-09-20	2006-12-13	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa
WO2006034341A2 (fr)	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Derives heterocycliques et leur utilisation en tant qu'agents therapeutiques
BRPI0515482A (pt)	2004-09-20	2008-07-22	Xenon Pharmaceuticals Inc	derivados heterocìclicos e seus usos como agentes terapêuticos
MX2007003327A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa.
CA2580855A1 (fr)	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Derives heterocycliques et leur utilisation en tant qu'agents therapeutiques
US8071603B2 (en)	2004-09-20	2011-12-06	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors
WO2006044456A1 (fr) *	2004-10-13	2006-04-27	Ptc Therapeutics, Inc.	Composes de suppression de non-sens et procedes de leur utilisation
US8541457B2 (en)	2005-06-03	2013-09-24	Xenon Pharmaceuticals Inc.	Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors
US7947707B2 (en) *	2005-10-07	2011-05-24	Kissei Pharmaceutical Co., Ltd.	Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same
CN101516387B (zh) *	2006-07-26	2014-06-04	桑多斯股份公司	卡泊芬净制剂
US8853392B2 (en)	2007-06-03	2014-10-07	Vanderbilt University	Benzamide mGluR5 positive allosteric modulators and methods of making and using same
EP2786993B1 (fr)	2007-08-13	2017-11-15	Monsanto Technology LLC	Procédé et compositions pour le contrôle de nématodes
TW200934507A (en) *	2007-10-29	2009-08-16	Astellas Pharma Inc	Polypeptide compounds
US8034806B2 (en)	2007-11-02	2011-10-11	Vanderbilt University	Bicyclic mGluR5 positive allosteric modulators and methods of making and using same
US8362050B2 (en) *	2008-06-24	2013-01-29	Irm Llc	Compounds and methods for modulating G protein-coupled receptors
US9394340B2 (en)	2009-03-24	2016-07-19	Cadila Healthcare Limited	Purification process for lipopeptides
BR112013023531A2 (pt)	2011-04-04	2016-12-06	Xellia Pharmaceuticals Aps	processo de um único vaso para a fabricação de micafungina ou de um sal desta
WO2012143293A1 (fr)	2011-04-20	2012-10-26	Xellia Pharmaceuticals Aps	Procédé de purification de la micafongine
CN102775476B (zh)	2011-05-12	2015-01-07	上海天伟生物制药有限公司	一种米卡芬净钠盐的制备方法
EP2709609B1 (fr)	2011-05-17	2017-10-04	Shionogi & Co., Ltd.	Composés hétérocycliques
EP2763971B1 (fr)	2011-09-09	2016-06-08	Sandoz AG	Préparation d'intermédiares de micafongine
CN102627689B (zh) *	2012-03-30	2014-08-06	上海天伟生物制药有限公司	一种环肽类化合物的水合物及其制备方法和用途
CN102627688B (zh)	2012-03-30	2014-12-31	上海天伟生物制药有限公司	一种高纯度环肽化合物及其制备方法和用途
CN102659930B (zh)	2012-03-30	2014-04-23	上海天伟生物制药有限公司	一种高纯度环肽类物质的晶体及其制备方法和用途
EP3150621A4 (fr) *	2014-05-29	2017-12-27	Shanghai Techwell Biopharmaceutical Co., Ltd	Composition de composé peptidique cyclique, son procédé de préparation et ses utilisations
WO2015180682A1 (fr) *	2014-05-29	2015-12-03	上海天伟生物制药有限公司	Solvate d'un composé peptidique cyclique, son procédé de préparation et ses utilisations
WO2016056023A2 (fr) *	2014-10-07	2016-04-14	Alaparthi Lakshmi Prasad	Produits intermédiaires et procédés de préparation de micafungine
CA2937365C (fr)	2016-03-29	2018-09-18	F. Hoffmann-La Roche Ag	Formulation en granules de 5-methyl-1-phenyl-2-(1h)-pyridone et methode de fabrication associee
PL3554474T3 (pl)	2016-12-16	2024-04-15	Baxter International Inc.	Kompozycje mykafunginy
EP3485873A1 (fr)	2017-11-17	2019-05-22	Cadila Healthcare Limited	Compositions injectables pharmaceutiques stables de micafungine
CN113087775B (zh) *	2018-05-31	2022-07-08	杭州中美华东制药有限公司	米卡芬净钠新晶型ii及其制备方法
WO2020013116A1 (fr) *	2018-07-10	2020-01-16	京都薬品工業株式会社	Inhibiteur de ptp-1b et son utilisation
CN110734408A (zh) *	2019-10-22	2020-01-31	重庆康乐制药有限公司	一种米卡芬净类衍生物侧链中间体的制备方法
CN115785226B (zh) *	2021-09-09	2026-02-24	上海天伟生物制药有限公司	一种棘白菌素药物杂质及其制备、纯化方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1574603A1 (ru) *	1988-08-11	1990-06-30	Ивановский Химико-Технологический Институт	Способ получени мезо-тетраарилоктаметилпорфиринов
IE912046A1 (en) *	1990-06-18	1991-12-18	Fujisawa Pharmaceutical Co	New polypeptide compound and a process for preparation¹thereof
IL122315A (en) *	1992-03-19	2002-03-10	Lilly Co Eli	Cyclic peptides and antifungal pharmaceutical compositions containing them

1995
- 1995-09-29 HU HU9800338A patent/HU228151B1/hu active Protection Beyond IP Right Term
- 1995-09-29 AU AU35780/95A patent/AU696949B2/en not_active Expired
- 1995-09-29 EP EP95932935A patent/EP0788511B1/fr not_active Expired - Lifetime
- 1995-09-29 CA CA002202058A patent/CA2202058C/fr not_active Expired - Lifetime
- 1995-09-29 MX MX9702531A patent/MX9702531A/es unknown
- 1995-09-29 KR KR1019970702213A patent/KR100353303B1/ko not_active Expired - Lifetime
- 1995-09-29 DE DE122008000025C patent/DE122008000025I2/de active Active
- 1995-09-29 PT PT95932935T patent/PT788511E/pt unknown
- 1995-09-29 AT AT95932935T patent/ATE229541T1/de active
- 1995-09-29 JP JP8512472A patent/JP2897427B2/ja not_active Expired - Lifetime
- 1995-09-29 DK DK95932935T patent/DK0788511T3/da active
- 1995-09-29 US US08/809,723 patent/US6107458A/en not_active Expired - Lifetime
- 1995-09-29 DE DE69529172T patent/DE69529172T2/de not_active Expired - Lifetime
- 1995-09-29 CN CNB95196643XA patent/CN1203089C/zh not_active Expired - Lifetime
- 1995-09-29 WO PCT/JP1995/001983 patent/WO1996011210A1/fr not_active Ceased
- 1995-09-29 RU RU97107338/04A patent/RU2165423C2/ru active Protection Beyond IP Right Term
- 1995-09-29 ES ES95932935T patent/ES2187575T3/es not_active Expired - Lifetime
- 1995-10-02 IL IL11548495A patent/IL115484A/xx not_active IP Right Cessation
- 1995-10-06 BR BRPI9504791-3A patent/BR9504791B1/pt active IP Right Grant
- 1995-10-06 TR TR95/01229A patent/TR199501229A2/xx unknown
- 1995-10-06 BR BRPI9504791A patent/BRPI9504791B8/pt not_active IP Right Cessation
- 1995-10-06 AR ARP9501333763A patent/AR041770A1/es unknown
1997
- 1997-04-04 FI FI971397A patent/FI119988B/fi not_active IP Right Cessation
- 1997-04-04 NO NO19971544A patent/NO328483B1/no not_active IP Right Cessation
- 1997-04-17 OA OA60989A patent/OA10475A/en unknown
1998
- 1998-05-19 JP JP13675698A patent/JP3518665B2/ja not_active Expired - Lifetime
1999
- 1999-02-11 US US09/248,267 patent/US6265536B1/en not_active Expired - Lifetime
2008
- 2008-06-03 NL NL300352C patent/NL300352I2/nl unknown
- 2008-06-04 LU LU91452C patent/LU91452I2/fr unknown
- 2008-06-27 FR FR08C0028C patent/FR08C0028I2/fr active Active
2010
- 2010-08-09 NO NO2010016C patent/NO2010016I2/no unknown

Also Published As

Publication number	Publication date
PT788511E (pt)	2003-04-30
DE122008000025I1 (de)	2008-08-21
HU228151B1 (en)	2012-12-28
IL115484A (en)	2000-07-16
JP2897427B2 (ja)	1999-05-31
LU91452I2 (fr)	2008-08-04
CA2202058A1 (fr)	1996-04-18
AR041770A1 (es)	2005-06-01
KR970707150A (ko)	1997-12-01
WO1996011210A1 (fr)	1996-04-18
MX9702531A (es)	1997-06-28
BR9504791B1 (pt)	2010-10-05
NL300352I2 (nl)	2008-11-03
CA2202058C (fr)	2007-11-06
BRPI9504791B8 (pt)	2019-12-31
DE69529172D1 (de)	2003-01-23
NL300352I1 (nl)	2008-08-01
FI971397L (fi)	1997-05-27
HUT77736A (hu)	1998-07-28
TR199501229A2 (tr)	1996-07-21
EP0788511B1 (fr)	2002-12-11
NO971544D0 (no)	1997-04-04
DE69529172T2 (de)	2003-04-17
ATE229541T1 (de)	2002-12-15
FI119988B (fi)	2009-05-29
AU3578095A (en)	1996-05-02
US6107458A (en)	2000-08-22
ES2187575T3 (es)	2003-06-16
NO328483B1 (no)	2010-03-01
NO2010016I1 (no)	2010-08-16
JPH10507174A (ja)	1998-07-14
CN1203089C (zh)	2005-05-25
BR9504791A (pt)	1996-10-22
FR08C0028I1 (fr)	2008-08-15
RU2165423C2 (ru)	2001-04-20
IL115484A0 (en)	1996-01-19
NO971544L (no)	1997-06-04
DE122008000025I2 (de)	2011-02-17
FR08C0028I2 (fr)	2009-11-20
FI971397A0 (fi)	1997-04-04
HK1004136A1 (en)	1998-11-20
EP0788511A1 (fr)	1997-08-13
US6265536B1 (en)	2001-07-24
DK0788511T3 (da)	2003-03-31
KR100353303B1 (ko)	2003-01-15
NO2010016I2 (no)	2011-10-17
JP3518665B2 (ja)	2004-04-12
AU696949B2 (en)	1998-09-24
JPH10324695A (ja)	1998-12-08
CN1168675A (zh)	1997-12-24

Publication	Publication Date	Title
OA10475A (en)	2002-04-08	Cyclic hexapeptides having antibiotic activity
CA2044746C (fr)	2001-08-07	Compose peptideque et son processus de preparation
JP3551469B2 (ja)	2004-08-04	新規ポリペプチド化合物及びその塩
WO1999040108A1 (fr)	1999-08-12	Nouveau compose
AU662522B2 (en)	1995-09-07	New peptide compound and a process for the preparation thereof
JP2004526728A (ja)	2004-09-02	抗菌活性を有する環状ヘキサペプチド化合物
US6743776B2 (en)	2004-06-01	Cyclohexapeptides having antimicrobial activity
JP3906690B2 (ja)	2007-04-18	環状ヘキサペプチド誘導体
US5952299A (en)	1999-09-14	Cyclic peptide nuclei and derivatives thereof
JP2005524640A (ja)	2005-08-18	新規化合物
AU756792B2 (en)	2003-01-23	New compound
IE921476A1 (en)	1992-11-18	New peptide compound and a process for the preparation¹thereof