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
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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
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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
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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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
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238000001990 intravenous administration Methods 0.000 description 4
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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
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238000000746 purification Methods 0.000 description 4
125000000714 pyrimidinyl group Chemical group 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
PVRFWXFHUOIQLV-UHFFFAOYSA-N 1-amino-3-(4-octylphenyl)urea Chemical compound CCCCCCCCC1=CC=C(NC(=O)NN)C=C1 PVRFWXFHUOIQLV-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
PWGPANWHHZDAIP-UHFFFAOYSA-N 3-[4-(4-pentylphenyl)phenyl]propanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(CCC(O)=O)C=C1 PWGPANWHHZDAIP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
241000206607 Porphyra umbilicalis Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
238000007918 intramuscular administration Methods 0.000 description 3
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
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239000003795 chemical substances by application Substances 0.000 description 2
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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
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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
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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
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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)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines Containing Material From Animals Or 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 (de)
EP (1)	EP0788511B1 (de)
JP (2)	JP2897427B2 (de)
KR (1)	KR100353303B1 (de)
CN (1)	CN1203089C (de)
AR (1)	AR041770A1 (de)
AT (1)	ATE229541T1 (de)
AU (1)	AU696949B2 (de)
BR (2)	BRPI9504791B8 (de)
CA (1)	CA2202058C (de)
DE (2)	DE69529172T2 (de)
DK (1)	DK0788511T3 (de)
ES (1)	ES2187575T3 (de)
FI (1)	FI119988B (de)
FR (1)	FR08C0028I2 (de)
HU (1)	HU228151B1 (de)
IL (1)	IL115484A (de)
LU (1)	LU91452I2 (de)
MX (1)	MX9702531A (de)
NL (1)	NL300352I2 (de)
NO (2)	NO328483B1 (de)
OA (1)	OA10475A (de)
PT (1)	PT788511E (de)
RU (1)	RU2165423C2 (de)
TR (1)	TR199501229A2 (de)
WO (1)	WO1996011210A1 (de)

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* Cited by examiner, † Cited by third party
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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
EP0994101A4 (de) *	1997-06-18	2002-05-02	Fujisawa Pharmaceutical Co	Neues herstellungsverfahren
IL137494A0 (en) *	1998-02-09	2001-07-24	Fujisawa Pharmaceutical Co	Polypeptide compounds, process for the preparation thereof and pharmaceutical compositions containing the same
AU756792B2 (en) *	1998-02-09	2003-01-23	Fujisawa Pharmaceutical Co., Ltd.	New compound
JP4854855B2 (ja) *	1999-02-11	2012-01-18	エミスフェアー・テクノロジーズ・インク	オキサジアゾール化合物及び活性剤をデリバリーするための組成物
US7084279B1 (en) *	1999-02-11	2006-08-01	Emisphere Technologies Inc.	Oxadiazole compounds and compositions for delivering active agents
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
US7166572B1 (en)	1999-07-27	2007-01-23	Aventis Pharma Deutschland Gmbh	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
EP1356816B1 (de)	2001-01-29	2009-12-23	Shionogi & Co., Ltd.	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
EP2316468A1 (de)	2002-02-22	2011-05-04	Shire LLC	Abgabesystem und Verfahren zum Schutz und zur Verabreichung von Dextroamphetamin
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
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1995
- 1995-09-29 US US08/809,723 patent/US6107458A/en not_active Expired - Lifetime
- 1995-09-29 HU HU9800338A patent/HU228151B1/hu active Protection Beyond IP Right Term
- 1995-09-29 PT PT95932935T patent/PT788511E/pt unknown
- 1995-09-29 CN CNB95196643XA patent/CN1203089C/zh not_active Expired - Lifetime
- 1995-09-29 EP EP95932935A patent/EP0788511B1/de not_active Expired - Lifetime
- 1995-09-29 WO PCT/JP1995/001983 patent/WO1996011210A1/en not_active Ceased
- 1995-09-29 JP JP8512472A patent/JP2897427B2/ja not_active Expired - Lifetime
- 1995-09-29 RU RU97107338/04A patent/RU2165423C2/ru active Protection Beyond IP Right Term
- 1995-09-29 AU AU35780/95A patent/AU696949B2/en not_active Expired
- 1995-09-29 AT AT95932935T patent/ATE229541T1/de active
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- 1995-09-29 DE DE69529172T patent/DE69529172T2/de not_active Expired - Lifetime
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- 1995-09-29 CA CA002202058A patent/CA2202058C/en not_active Expired - Lifetime
- 1995-09-29 DK DK95932935T patent/DK0788511T3/da active
- 1995-09-29 DE DE122008000025C patent/DE122008000025I2/de active Active
- 1995-09-29 KR KR1019970702213A patent/KR100353303B1/ko not_active Expired - Lifetime
- 1995-10-02 IL IL11548495A patent/IL115484A/xx not_active IP Right Cessation
- 1995-10-06 BR BRPI9504791A patent/BRPI9504791B8/pt not_active IP Right Cessation
- 1995-10-06 TR TR95/01229A patent/TR199501229A2/xx unknown
- 1995-10-06 BR BRPI9504791-3A patent/BR9504791B1/pt active IP Right Grant
- 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
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1998
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1999
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2008
- 2008-06-03 NL NL300352C patent/NL300352I2/nl unknown
- 2008-06-04 LU LU91452C patent/LU91452I2/fr unknown
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Also Published As

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

Publication	Publication Date	Title
OA10475A (en)	2002-04-08	Cyclic hexapeptides having antibiotic activity
CA2044746C (en)	2001-08-07	Polypeptide compound and a process for preparation thereof
JP3551469B2 (ja)	2004-08-04	新規ポリペプチド化合物及びその塩
WO1999040108A1 (en)	1999-08-12	New compound
AU662522B2 (en)	1995-09-07	New peptide compound and a process for the preparation thereof
JPH05966A (ja)	1993-01-08	ポリペプチド化合物の新規用途
US20050261177A1 (en)	2005-11-24	Compound
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