NO884362L - Isoksazolidin-derivater. - Google Patents
Isoksazolidin-derivater.Info
- Publication number
- NO884362L NO884362L NO88884362A NO884362A NO884362L NO 884362 L NO884362 L NO 884362L NO 88884362 A NO88884362 A NO 88884362A NO 884362 A NO884362 A NO 884362A NO 884362 L NO884362 L NO 884362L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- methyl
- substituted
- lower alkyl
- imidazol
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- -1 phenylthiomethyl groups Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000005504 styryl group Chemical group 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- YQXIHRACWMECSF-UHFFFAOYSA-N 2-benzyl-5-[(4-chlorophenoxy)methyl]-3-(imidazol-1-ylmethyl)-3-phenyl-1,2-oxazolidine Chemical compound C1=CC(Cl)=CC=C1OCC1ON(CC=2C=CC=CC=2)C(CN2C=NC=C2)(C=2C=CC=CC=2)C1 YQXIHRACWMECSF-UHFFFAOYSA-N 0.000 claims description 2
- YDUPITMGJWVNDC-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-2-methyl-3-naphthalen-2-yl-5-phenyl-1,2-oxazolidine Chemical compound CN1OC(C=2C=CC=CC=2)CC1(C=1C=C2C=CC=CC2=CC=1)CN1C=CN=C1 YDUPITMGJWVNDC-UHFFFAOYSA-N 0.000 claims description 2
- CXTDTFACBQJPPB-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-(imidazol-1-ylmethyl)-2,5-dimethyl-3-phenyl-1,2-oxazolidine Chemical compound CN1OC(C)(C=2C=CC(Cl)=CC=2)CC1(C=1C=CC=CC=1)CN1C=CN=C1 CXTDTFACBQJPPB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000003480 eluent Substances 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 229940125898 compound 5 Drugs 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 150000002546 isoxazolidines Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- FZENGILVLUJGJX-UHFFFAOYSA-N acetaldehyde oxime Chemical compound CC=NO FZENGILVLUJGJX-UHFFFAOYSA-N 0.000 description 6
- 229940125773 compound 10 Drugs 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 5
- KWXDOKLIYYAHJN-UHFFFAOYSA-N 1-chloro-4-prop-2-enoxybenzene Chemical compound ClC1=CC=C(OCC=C)C=C1 KWXDOKLIYYAHJN-UHFFFAOYSA-N 0.000 description 4
- CVJNXVLQSKPUGP-UHFFFAOYSA-N 2-imidazol-1-yl-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CN1C=CN=C1 CVJNXVLQSKPUGP-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AWFKWSSQKRKAER-UHFFFAOYSA-N 1-methoxy-4-prop-2-enoxybenzene Chemical compound COC1=CC=C(OCC=C)C=C1 AWFKWSSQKRKAER-UHFFFAOYSA-N 0.000 description 3
- RXGNQUOYJPSWRW-UHFFFAOYSA-N 1-phenyl-2-(1,2,4-triazol-1-yl)ethanone Chemical compound C=1C=CC=CC=1C(=O)CN1C=NC=N1 RXGNQUOYJPSWRW-UHFFFAOYSA-N 0.000 description 3
- VNZJFZNORMTWIB-UHFFFAOYSA-N 2-imidazol-1-yl-n-methyl-1-naphthalen-2-ylethanimine oxide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=[N+]([O-])C)CN1C=CN=C1 VNZJFZNORMTWIB-UHFFFAOYSA-N 0.000 description 3
- QAALEXJCRCMAAC-UHFFFAOYSA-N 2-imidazol-1-yl-n-methyl-1-phenylethanimine oxide Chemical compound C=1C=CC=CC=1C(=[N+]([O-])C)CN1C=CN=C1 QAALEXJCRCMAAC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WYDABHVBJIIVJN-UHFFFAOYSA-N 3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=NC=NN1CC1CCON1 WYDABHVBJIIVJN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XZKRXPZXQLARHH-XVNBXDOJSA-N [(1e)-buta-1,3-dienyl]benzene Chemical compound C=C\C=C\C1=CC=CC=C1 XZKRXPZXQLARHH-XVNBXDOJSA-N 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 description 2
- OMIKSWCLTOQKCB-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.ONCC1=CC=CC(Cl)=C1 OMIKSWCLTOQKCB-UHFFFAOYSA-N 0.000 description 2
- CZPYPWDKUTWCHV-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CNO)C=C1 CZPYPWDKUTWCHV-UHFFFAOYSA-N 0.000 description 2
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical class ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009885 systemic effect Effects 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
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SFAFRNPNMNDVJH-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-imidazol-1-yl-n-methylethanimine oxide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=[N+]([O-])C)CN1C=CN=C1 SFAFRNPNMNDVJH-UHFFFAOYSA-N 0.000 description 1
- BCRAHCZQQQCKGY-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-imidazol-1-yl-n-methylethanimine oxide Chemical compound C=1C=C(Cl)C=CC=1C(=[N+]([O-])C)CN1C=CN=C1 BCRAHCZQQQCKGY-UHFFFAOYSA-N 0.000 description 1
- PWFVNVYRKXDPGV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-imidazol-1-ylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CN1C=NC=C1 PWFVNVYRKXDPGV-UHFFFAOYSA-N 0.000 description 1
- WUHGMWIWIMMDKW-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-imidazol-1-ylethanone Chemical compound C1=CC(F)=CC=C1C(=O)CN1C=NC=C1 WUHGMWIWIMMDKW-UHFFFAOYSA-N 0.000 description 1
- WQDGTJOEMPEHHL-UHFFFAOYSA-N 1-chloro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(Cl)C=C1 WQDGTJOEMPEHHL-UHFFFAOYSA-N 0.000 description 1
- XCTSGGVBLWBSIJ-UHFFFAOYSA-N 1-methoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=CC=C(C(C)=C)C=C1 XCTSGGVBLWBSIJ-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- DKLIVMUSYMTQSF-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1-phenylethanone Chemical class C=1C=CC=CC=1C(=O)CC1=NC=CN1 DKLIVMUSYMTQSF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- SEXDJCQEJSPJLL-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-3-(4-methylphenyl)-5-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(C)=CC=C1C1(CN2N=CN=C2)N(CC=2C=C(Cl)C=CC=2)OC(C=2C=CC=CC=2)C1 SEXDJCQEJSPJLL-UHFFFAOYSA-N 0.000 description 1
- DLGIMFQUJQFEOK-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-3-(imidazol-1-ylmethyl)-5-[(4-methylphenyl)sulfanylmethyl]-3-phenyl-1,2-oxazolidine Chemical compound C1=CC(C)=CC=C1SCC1ON(CC=2C=CC(F)=CC=2)C(CN2C=NC=C2)(C=2C=CC=CC=2)C1 DLGIMFQUJQFEOK-UHFFFAOYSA-N 0.000 description 1
- VGWJMEXTYGIEIO-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-5-[(4-methylphenyl)sulfanylmethyl]-3-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(C)=CC=C1SCC1ON(CC=2C=CC(F)=CC=2)C(CN2N=CN=C2)(C=2C=CC=CC=2)C1 VGWJMEXTYGIEIO-UHFFFAOYSA-N 0.000 description 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 1
- QHJWHJUHIMFMQC-UHFFFAOYSA-N 2-benzyl-3-(4-fluorophenyl)-5-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(F)=CC=C1C1(CN2N=CN=C2)N(CC=2C=CC=CC=2)OC(C=2C=CC=CC=2)C1 QHJWHJUHIMFMQC-UHFFFAOYSA-N 0.000 description 1
- BAFDYTDBFCDIAE-UHFFFAOYSA-N 2-benzyl-5-[(4-chlorophenoxy)methyl]-3-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(Cl)=CC=C1OCC1ON(CC=2C=CC=CC=2)C(CN2N=CN=C2)(C=2C=CC=CC=2)C1 BAFDYTDBFCDIAE-UHFFFAOYSA-N 0.000 description 1
- SOVGCBAUEMQUHG-UHFFFAOYSA-N 2-methyl-3,5,5-triphenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound CN1OC(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1(C=1C=CC=CC=1)CN1C=NC=N1 SOVGCBAUEMQUHG-UHFFFAOYSA-N 0.000 description 1
- FNCYBKAIHZMQKS-UHFFFAOYSA-N 2-methyl-3-naphthalen-2-yl-5-(phenoxymethyl)-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2N=CN=C2)N(C)OC1COC1=CC=CC=C1 FNCYBKAIHZMQKS-UHFFFAOYSA-N 0.000 description 1
- CCFXQDDRHXPPPV-UHFFFAOYSA-N 2-methyl-3-naphthalen-2-yl-5-(phenylsulfanylmethyl)-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2N=CN=C2)N(C)OC1CSC1=CC=CC=C1 CCFXQDDRHXPPPV-UHFFFAOYSA-N 0.000 description 1
- GDCCBWPNGNJHPP-SDNWHVSQSA-N 2-methyl-3-naphthalen-2-yl-5-[(e)-2-phenylethenyl]-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound CN1OC(\C=C\C=2C=CC=CC=2)CC1(C=1C=C2C=CC=CC2=CC=1)CN1C=NC=N1 GDCCBWPNGNJHPP-SDNWHVSQSA-N 0.000 description 1
- MAOYOAAYVFEIDW-UHFFFAOYSA-N 3-(4-chloro-3-methylphenyl)-2-[(4-chloro-3-methylphenyl)methyl]-5-(4-methoxyphenyl)-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1ON(CC=2C=C(C)C(Cl)=CC=2)C(CN2N=CN=C2)(C=2C=C(C)C(Cl)=CC=2)C1 MAOYOAAYVFEIDW-UHFFFAOYSA-N 0.000 description 1
- ANRZAZLKVWZLCX-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[(4-methoxyphenyl)methyl]-5-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1CN1C(C=2C=CC(Cl)=CC=2)(CN2N=CN=C2)CC(C=2C=CC=CC=2)O1 ANRZAZLKVWZLCX-UHFFFAOYSA-N 0.000 description 1
- LDRKYQKCDQZAFV-LFIBNONCSA-N 3-(4-fluorophenyl)-2-[(4-methylphenyl)methyl]-5-[(e)-2-phenylethenyl]-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(C)=CC=C1CN1C(C=2C=CC(F)=CC=2)(CN2N=CN=C2)CC(\C=C\C=2C=CC=CC=2)O1 LDRKYQKCDQZAFV-LFIBNONCSA-N 0.000 description 1
- DJEXREZHXAPORE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-[(4-methylphenyl)methyl]-5-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1(CN2N=CN=C2)N(CC=2C=CC(C)=CC=2)OC(C=2C=CC=CC=2)C1 DJEXREZHXAPORE-UHFFFAOYSA-N 0.000 description 1
- KDKCYWCNLSCEOS-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-2-methyl-3,5,5-triphenyl-1,2-oxazolidine Chemical compound CN1OC(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1(C=1C=CC=CC=1)CN1C=CN=C1 KDKCYWCNLSCEOS-UHFFFAOYSA-N 0.000 description 1
- ZNVJSYDUTRAKKI-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-2-methyl-3-naphthalen-2-yl-5-(phenoxymethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2C=NC=C2)N(C)OC1COC1=CC=CC=C1 ZNVJSYDUTRAKKI-UHFFFAOYSA-N 0.000 description 1
- BCCVDIDBDTUXGR-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-2-methyl-3-naphthalen-2-yl-5-(phenylsulfanylmethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2C=NC=C2)N(C)OC1CSC1=CC=CC=C1 BCCVDIDBDTUXGR-UHFFFAOYSA-N 0.000 description 1
- BGYKUMZMDMUBOB-SDNWHVSQSA-N 3-(imidazol-1-ylmethyl)-2-methyl-3-naphthalen-2-yl-5-[(e)-2-phenylethenyl]-1,2-oxazolidine Chemical compound CN1OC(\C=C\C=2C=CC=CC=2)CC1(C=1C=C2C=CC=CC2=CC=1)CN1C=CN=C1 BGYKUMZMDMUBOB-SDNWHVSQSA-N 0.000 description 1
- VQMRLXYDKSICTC-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-3-(4-methoxyphenyl)-2,5-dimethyl-5-phenyl-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1(CN2C=NC=C2)N(C)OC(C)(C=2C=CC=CC=2)C1 VQMRLXYDKSICTC-UHFFFAOYSA-N 0.000 description 1
- UPCNVJVQLKYWMI-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-5-(4-methoxyphenyl)-2,5-dimethyl-3-(4-methylphenyl)-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1(C)ON(C)C(CN2C=NC=C2)(C=2C=CC(C)=CC=2)C1 UPCNVJVQLKYWMI-UHFFFAOYSA-N 0.000 description 1
- QPSPQZOMEAHKQA-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)-5-[(4-methoxyphenoxy)methyl]-2-methyl-3-naphthalen-2-yl-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1OCC1ON(C)C(CN2C=NC=C2)(C=2C=C3C=CC=CC3=CC=2)C1 QPSPQZOMEAHKQA-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
- BPVVTRJJQZINNG-UHFFFAOYSA-N 4-chloro-1-ethenyl-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1C=C BPVVTRJJQZINNG-UHFFFAOYSA-N 0.000 description 1
- IWPQZAGFZZCTKC-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-3-(imidazol-1-ylmethyl)-3-(4-methoxyphenyl)-2,5-dimethyl-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1(CN2C=NC=C2)N(C)OC(C)(C=2C=C(Cl)C(Cl)=CC=2)C1 IWPQZAGFZZCTKC-UHFFFAOYSA-N 0.000 description 1
- RGUIRKVLGJKHHG-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-(imidazol-1-ylmethyl)-2,5-dimethyl-3-(4-methylphenyl)-1,2-oxazolidine Chemical compound C1=C(OC)C(OC)=CC=C1C1(C)ON(C)C(CN2C=NC=C2)(C=2C=CC(C)=CC=2)C1 RGUIRKVLGJKHHG-UHFFFAOYSA-N 0.000 description 1
- ZPCDPPOJMDKTLL-UHFFFAOYSA-N 5-(4-chlorophenyl)-2,5-dimethyl-3-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound CN1OC(C)(C=2C=CC(Cl)=CC=2)CC1(C=1C=CC=CC=1)CN1C=NC=N1 ZPCDPPOJMDKTLL-UHFFFAOYSA-N 0.000 description 1
- VEWVLMNIKNRVJS-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-methyl-3-naphthalen-2-yl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound CN1OC(C=2C=CC(Cl)=CC=2)CC1(C=1C=C2C=CC=CC2=CC=1)CN1C=NC=N1 VEWVLMNIKNRVJS-UHFFFAOYSA-N 0.000 description 1
- NQKTXEAJMFKXAY-UHFFFAOYSA-N 5-[(4-chlorophenoxy)methyl]-2-[(3-chlorophenyl)methyl]-3-(imidazol-1-ylmethyl)-3-phenyl-1,2-oxazolidine Chemical compound C1=CC(Cl)=CC=C1OCC1ON(CC=2C=C(Cl)C=CC=2)C(CN2C=NC=C2)(C=2C=CC=CC=2)C1 NQKTXEAJMFKXAY-UHFFFAOYSA-N 0.000 description 1
- WYIFYUPNUXQSGB-UHFFFAOYSA-N 5-[(4-chlorophenoxy)methyl]-2-[(3-chlorophenyl)methyl]-3-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(Cl)=CC=C1OCC1ON(CC=2C=C(Cl)C=CC=2)C(CN2N=CN=C2)(C=2C=CC=CC=2)C1 WYIFYUPNUXQSGB-UHFFFAOYSA-N 0.000 description 1
- AZKSKRYCXCTGAY-UHFFFAOYSA-N 5-[(4-chlorophenoxy)methyl]-2-methyl-3-naphthalen-2-yl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2N=CN=C2)N(C)OC1COC1=CC=C(Cl)C=C1 AZKSKRYCXCTGAY-UHFFFAOYSA-N 0.000 description 1
- NFRDCBVUADYHGT-UHFFFAOYSA-N 5-[(4-chlorophenoxy)methyl]-3-(imidazol-1-ylmethyl)-2-methyl-3-naphthalen-2-yl-1,2-oxazolidine Chemical compound C1C(C=2C=C3C=CC=CC3=CC=2)(CN2C=NC=C2)N(C)OC1COC1=CC=C(Cl)C=C1 NFRDCBVUADYHGT-UHFFFAOYSA-N 0.000 description 1
- DWRKRPRDUPCNHQ-UHFFFAOYSA-N 5-[(4-methoxyphenoxy)methyl]-2-methyl-3-naphthalen-2-yl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound C1=CC(OC)=CC=C1OCC1ON(C)C(CN2N=CN=C2)(C=2C=C3C=CC=CC3=CC=2)C1 DWRKRPRDUPCNHQ-UHFFFAOYSA-N 0.000 description 1
- ULTAFLBHGBXTSA-UHFFFAOYSA-N 5-hexyl-2-methyl-3-naphthalen-2-yl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine Chemical compound CN1OC(CCCCCC)CC1(C=1C=C2C=CC=CC2=CC=1)CN1N=CN=C1 ULTAFLBHGBXTSA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XBKGISUKTXMMEY-UHFFFAOYSA-N C1=C(Cl)C(C)=CC(C(CN2C=NC=C2)=[N+](C)[O-])=C1 Chemical compound C1=C(Cl)C(C)=CC(C(CN2C=NC=C2)=[N+](C)[O-])=C1 XBKGISUKTXMMEY-UHFFFAOYSA-N 0.000 description 1
- RKPSHUMAEAKELZ-UHFFFAOYSA-N C1=CC(C)=CC=C1C(=[N+](C)[O-])CN1C=NC=C1 Chemical compound C1=CC(C)=CC=C1C(=[N+](C)[O-])CN1C=NC=C1 RKPSHUMAEAKELZ-UHFFFAOYSA-N 0.000 description 1
- OGNRSBTUOMTXFH-UHFFFAOYSA-N C1=CC(OC)=CC=C1C(=[N+](C)[O-])CN1C=NC=C1 Chemical compound C1=CC(OC)=CC=C1C(=[N+](C)[O-])CN1C=NC=C1 OGNRSBTUOMTXFH-UHFFFAOYSA-N 0.000 description 1
- NITYEMKWIILBJU-UHFFFAOYSA-N C1=CN=CN1CC(C=1C=CC=CC=1)=[N+]([O-])CC1=CC=C(F)C=C1 Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)=[N+]([O-])CC1=CC=C(F)C=C1 NITYEMKWIILBJU-UHFFFAOYSA-N 0.000 description 1
- BIIZKMZTGRJDSH-UHFFFAOYSA-N C1=CN=CN1CC(C=1C=CC=CC=1)=[N+]([O-])CC1=CC=CC(Cl)=C1 Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)=[N+]([O-])CC1=CC=CC(Cl)=C1 BIIZKMZTGRJDSH-UHFFFAOYSA-N 0.000 description 1
- DGQUXEMIEBOZTC-UHFFFAOYSA-N C=1C=C(F)C=CC=1C(=[N+]([O-])C)CN1C=CN=C1 Chemical compound C=1C=C(F)C=CC=1C(=[N+]([O-])C)CN1C=CN=C1 DGQUXEMIEBOZTC-UHFFFAOYSA-N 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000893980 Microsporum canis Species 0.000 description 1
- VJQMLUBUZAGVPI-UHFFFAOYSA-N N-methyl-1-naphthalen-2-yl-2-(1,2,4-triazol-1-yl)ethanimine oxide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=[N+]([O-])C)CN1C=NC=N1 VJQMLUBUZAGVPI-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241001480046 Trichophyton schoenleinii Species 0.000 description 1
- 241001480048 Trichophyton tonsurans Species 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UTXWIODXVMKQGK-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-2,5-dimethyl-3-(1,2,4-triazol-1-ylmethyl)-1,2-oxazolidine-5-carboxylate Chemical compound CN1OC(C(=O)OC)(C)CC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 UTXWIODXVMKQGK-UHFFFAOYSA-N 0.000 description 1
- AJGHVEJPCLBASZ-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-3-(imidazol-1-ylmethyl)-2,5-dimethyl-1,2-oxazolidine-5-carboxylate Chemical compound CN1OC(C(=O)OC)(C)CC1(C=1C=CC(Cl)=CC=1)CN1C=NC=C1 AJGHVEJPCLBASZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- OERSFCWDCVETCJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]hydroxylamine Chemical compound ONCC1=CC=C(F)C=C1 OERSFCWDCVETCJ-UHFFFAOYSA-N 0.000 description 1
- FHWYUKDMBOYXCD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.ONCC1=CC=C(F)C=C1 FHWYUKDMBOYXCD-UHFFFAOYSA-N 0.000 description 1
- OBDCSLBLASRVMI-UHFFFAOYSA-N n-benzyl-2-imidazol-1-yl-1-phenylethanimine oxide Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)=[N+]([O-])CC1=CC=CC=C1 OBDCSLBLASRVMI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QGNRLAFFKKBSIM-UHFFFAOYSA-N prop-2-enylsulfanylbenzene Chemical compound C=CCSC1=CC=CC=C1 QGNRLAFFKKBSIM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/104,701 US4785117A (en) | 1987-10-02 | 1987-10-02 | 5,5-disubstituted-3-phenyl-3-phenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2-methylisoxazolidine derivatives (IR 3012) |
| US07/104,747 US4749793A (en) | 1987-10-02 | 1987-10-02 | 5-substituted-3-phenyl-3-[1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl]-2-benzylisoxazolidines (ir 3011) |
| US07/104,692 US4777263A (en) | 1987-10-02 | 1987-10-02 | 5-substituted-3-(2-naphthalenyl)-3-((1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl))-2-methylisoxazolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO884362D0 NO884362D0 (no) | 1988-09-30 |
| NO884362L true NO884362L (no) | 1989-04-03 |
Family
ID=27379794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO88884362A NO884362L (no) | 1987-10-02 | 1988-09-30 | Isoksazolidin-derivater. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0310061A1 (xx) |
| JP (1) | JPH01128981A (xx) |
| KR (1) | KR890006634A (xx) |
| AU (1) | AU2289888A (xx) |
| DK (1) | DK547388A (xx) |
| FI (1) | FI884520A (xx) |
| IL (1) | IL87797A0 (xx) |
| NO (1) | NO884362L (xx) |
| PT (1) | PT88653A (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ221116A (en) * | 1986-08-27 | 1990-01-29 | Pennwalt Corp | 3-phenyl-3-(1h-1,2,4-triazol-1-ylmethyl)-5-substituted-2-methylisoxazolidines |
| FR3012458B1 (fr) | 2013-10-25 | 2015-10-30 | Michelin & Cie | Composition de caoutchouc comprenant un additif compose 1,3-dipolaire portant une fonction imidazole |
| FR3012451B1 (fr) | 2013-10-25 | 2016-11-11 | Michelin & Cie | Compose 1,3-dipolaire portant une fonction imidazole |
| FR3012460B1 (fr) | 2013-10-25 | 2015-12-11 | Michelin & Cie | Composition de caoutchouc comprenant un elastomere dienique portant des fonctions imidazole reparties de facon aleatoire le long de la chaine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870094A (en) * | 1984-05-02 | 1989-09-26 | Uniroyal Chemical Company, Inc. | Substituted imidazoles and triazoles |
| ATE67493T1 (de) * | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
| NZ221116A (en) * | 1986-08-27 | 1990-01-29 | Pennwalt Corp | 3-phenyl-3-(1h-1,2,4-triazol-1-ylmethyl)-5-substituted-2-methylisoxazolidines |
| IL83436A0 (en) * | 1986-08-27 | 1988-01-31 | Pennwalt Corp | 5-substituted-3-phenyl-3-(1h-imidazol-1-ylmethyl)-2-methylisoxazolidines |
-
1988
- 1988-09-19 IL IL87797A patent/IL87797A0/xx unknown
- 1988-09-28 JP JP63241182A patent/JPH01128981A/ja active Pending
- 1988-09-28 AU AU22898/88A patent/AU2289888A/en not_active Abandoned
- 1988-09-29 EP EP88116061A patent/EP0310061A1/en not_active Withdrawn
- 1988-09-30 NO NO88884362A patent/NO884362L/no unknown
- 1988-09-30 KR KR1019880012725A patent/KR890006634A/ko not_active Application Discontinuation
- 1988-09-30 FI FI884520A patent/FI884520A/fi not_active Application Discontinuation
- 1988-09-30 PT PT88653A patent/PT88653A/pt not_active Application Discontinuation
- 1988-09-30 DK DK547388A patent/DK547388A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK547388D0 (da) | 1988-09-30 |
| FI884520A (fi) | 1989-04-03 |
| FI884520A0 (fi) | 1988-09-30 |
| PT88653A (pt) | 1989-07-31 |
| AU2289888A (en) | 1989-04-06 |
| IL87797A0 (en) | 1989-03-31 |
| JPH01128981A (ja) | 1989-05-22 |
| EP0310061A1 (en) | 1989-04-05 |
| KR890006634A (ko) | 1989-06-14 |
| NO884362D0 (no) | 1988-09-30 |
| DK547388A (da) | 1989-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5716969A (en) | Azolylamine derivative | |
| HU211474A9 (en) | Azole compounds, their production and use | |
| US4719306A (en) | Substituted 3,5-diphenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines | |
| DK145644B (da) | Analogifremgangsmaade til fremstilling af imidazolforbindelser | |
| US4723021A (en) | Substituted 5-(phenoxyalkyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines | |
| FR2542315A1 (fr) | Nouveaux composes azoliques, leur preparation et leur utilisation comme antifongiques et fongicides | |
| He et al. | Synthesis and biological activities of novel bis‐heterocyclic pyrrodiazole derivatives | |
| KR870001379B1 (ko) | 트리아졸 유도체의 제조방법 | |
| NO884362L (no) | Isoksazolidin-derivater. | |
| NO165104B (no) | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1, 1-disubstituerte cyklopropanderivater. | |
| NO873606L (no) | Nye alfa-substituerte ketonitron-derivater. | |
| US4749793A (en) | 5-substituted-3-phenyl-3-[1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl]-2-benzylisoxazolidines (ir 3011) | |
| RU2703997C1 (ru) | Гибридные амиды на основе триазола и тиазолидина, обладающие антимикробной активностью | |
| US4777263A (en) | 5-substituted-3-(2-naphthalenyl)-3-((1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl))-2-methylisoxazolidines | |
| US4785117A (en) | 5,5-disubstituted-3-phenyl-3-phenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2-methylisoxazolidine derivatives (IR 3012) | |
| US4727156A (en) | 3-(Substituted phenyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-5-{[(substituted phenyl)thio]me}isoxazolidine derivatives | |
| US4777264A (en) | 5-carbonyl derivatives of 3-phenyl-3-(1H-imadazol-1-ylmethyl)-2-methylisoxazolidines and related compounds thereof | |
| US4835283A (en) | 3,5-diphenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2 | |
| US4754042A (en) | 5-{[naphthyl(or 2-oxo-1,3-benzoxathiol-6-yl)oxy]methyl}-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines | |
| US4769470A (en) | 5-(phenyl or phenoxyalkyl)-3-(2-thienyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines | |
| US4769471A (en) | Substituted 3,5-diphenyl-3-(1H-1,2,4-triazol-1-yl-methyl)-2-methylisoxazolidines | |
| US4777262A (en) | 5-(substituted thiomethyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine derivatives | |
| EP0257391A2 (en) | 5-Substituted-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines | |
| NO884360L (no) | Substituerte 2-metylisoksazolidiner. | |
| NO169071B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 3-fenyl-3-(1h-1,2,4-triazol-1-ylmetyl)-5-substituerte-2-metylisoxazolidiner |