CH636886A5 - Verfahren zur herstellung von antibiotisch wirksamen, ungesaettigten oder substituierten methylaethern. - Google Patents
Verfahren zur herstellung von antibiotisch wirksamen, ungesaettigten oder substituierten methylaethern. Download PDFInfo
- Publication number
- CH636886A5 CH636886A5 CH1085377A CH1085377A CH636886A5 CH 636886 A5 CH636886 A5 CH 636886A5 CH 1085377 A CH1085377 A CH 1085377A CH 1085377 A CH1085377 A CH 1085377A CH 636886 A5 CH636886 A5 CH 636886A5
- Authority
- CH
- Switzerland
- Prior art keywords
- papulacandin
- ether
- group
- radical
- mono
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000005217 methyl ethers Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 258
- -1 carbonylmethyl Chemical group 0.000 claims description 158
- 108010058641 papulacandins Proteins 0.000 claims description 127
- XKSZJTQIZHUMGA-KDCKXVQZSA-N [(3'r,4's,5'r,6'r)-3',4,5',6-tetrahydroxy-6'-(hydroxymethyl)spiro[1h-2-benzofuran-3,2'-oxane]-4'-yl] (2e,4e,8e,10e)-7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate Chemical compound O[C@@H]1[C@@H](OC(=O)/C=C/C=C/CC(O)C(/C)=C/C=C/CCC(C)CC)[C@H](O)[C@@H](CO)OC11C2=C(O)C=C(O)C=C2CO1 XKSZJTQIZHUMGA-KDCKXVQZSA-N 0.000 claims description 97
- 229930186782 Papulacandin Natural products 0.000 claims description 95
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 91
- UJLFRJFJTPPIOK-XALDCVGDSA-N Papulacandin B Natural products CCC(C)CCC=CC=C(/C)C(O)CC=CC=CC(=O)OC1C(O)C2(OCc3cc(O)cc(O)c23)OC(CO)C1OC4OC(COC(=O)C=CC=C/C=C/C(O)CC)C(O)C(O)C4O UJLFRJFJTPPIOK-XALDCVGDSA-N 0.000 claims description 45
- UJLFRJFJTPPIOK-RZGJRGQUSA-N papulacandin b Chemical compound O([C@@H]1[C@@H](CO)O[C@@]2(C3=C(O)C=C(O)C=C3CO2)[C@H](O)[C@H]1OC(=O)/C=C/C=C/C[C@H](O)C(/C)=C/C=C/CC[C@@H](C)CC)[C@@H]1O[C@H](COC(=O)\C=C\C=C/C=C/C(O)CC)[C@H](O)[C@H](O)[C@H]1O UJLFRJFJTPPIOK-RZGJRGQUSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- DPVWBQZOSHCQTG-NVTMJBNDSA-N papulacandin A Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](COC(=O)/C=C/C=C/CCCCC)O[C@H]1O[C@H]1[C@H](OC(=O)\C=C\C=C\C[C@H](O)C(\C)=C\C=C\CC[C@@H](C)CC)[C@@H](O)[C@]2(C3=C(O)C=C(O)C=C3CO2)O[C@@H]1CO DPVWBQZOSHCQTG-NVTMJBNDSA-N 0.000 claims description 27
- DPVWBQZOSHCQTG-UHFFFAOYSA-N Papulacandin A Natural products OC1C(O)C(O)C(COC(=O)C=CC=CCCCCC)OC1OC1C(OC(=O)C=CC=CCC(O)C(C)=CC=CCCC(C)CC)C(O)C2(C3=C(O)C=C(O)C=C3CO2)OC1CO DPVWBQZOSHCQTG-UHFFFAOYSA-N 0.000 claims description 26
- 230000003115 biocidal effect Effects 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000007858 starting material Substances 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000001033 ether group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000002170 ethers Chemical class 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000036961 partial effect Effects 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 150000003672 ureas Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 241000222122 Candida albicans Species 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229940095731 candida albicans Drugs 0.000 claims description 5
- KUCRTUQUAYLJDC-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethoxy)acetate Chemical compound COC(=O)COCC(=O)OC KUCRTUQUAYLJDC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- UJLFRJFJTPPIOK-UHFFFAOYSA-N Papulacandin C Natural products CCC(C)CCC=CC=C(C)C(O)CC=CC=CC(=O)OC1C(O)C2(C3=C(O)C=C(O)C=C3CO2)OC(CO)C1OC1OC(COC(=O)C=CC=CC=CC(O)CC)C(O)C(O)C1O UJLFRJFJTPPIOK-UHFFFAOYSA-N 0.000 claims description 2
- XKSZJTQIZHUMGA-UHFFFAOYSA-N Papulacandin D Natural products OC1C(OC(=O)C=CC=CCC(O)C(C)=CC=CCCC(C)CC)C(O)C(CO)OC11C2=C(O)C=C(O)C=C2CO1 XKSZJTQIZHUMGA-UHFFFAOYSA-N 0.000 claims description 2
- 206010033733 Papule Diseases 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- UJLFRJFJTPPIOK-JPWNLYTBSA-N papulacandin C Chemical compound O([C@@H]1[C@@H](CO)O[C@@]2(C3=C(O)C=C(O)C=C3CO2)[C@H](O)[C@H]1OC(=O)/C=C/C=C/C[C@H](O)C(/C)=C/C=C/CC[C@@H](C)CC)[C@@H]1O[C@H](COC(=O)\C=C\C=C\C=C\C(O)CC)[C@H](O)[C@H](O)[C@H]1O UJLFRJFJTPPIOK-JPWNLYTBSA-N 0.000 claims description 2
- XKSZJTQIZHUMGA-HPZFVNCBSA-N papulacandin D Chemical compound O[C@@H]1[C@@H](OC(=O)/C=C/C=C/C[C@H](O)C(/C)=C/C=C/CC[C@@H](C)CC)[C@H](O)[C@@H](CO)O[C@@]11C2=C(O)C=C(O)C=C2CO1 XKSZJTQIZHUMGA-HPZFVNCBSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 230000037213 diet Effects 0.000 claims 2
- 235000005911 diet Nutrition 0.000 claims 2
- 241000364057 Peoria Species 0.000 claims 1
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzylether Substances C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 86
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 44
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000843 powder Substances 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 28
- 239000003480 eluent Substances 0.000 description 25
- 239000012043 crude product Substances 0.000 description 24
- 239000012071 phase Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 19
- 229910001923 silver oxide Inorganic materials 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
- 235000015097 nutrients Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 235000011054 acetic acid Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000003776 cleavage reaction Methods 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 230000007017 scission Effects 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 150000002366 halogen compounds Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- DAUJNGCWXSFRIM-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-[(4-nitrophenyl)methoxy]-2-oxoethoxy]acetate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)COCC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 DAUJNGCWXSFRIM-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
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- 238000001556 precipitation Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
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- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 2
- 241000222178 Candida tropicalis Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical class OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000013587 production medium Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 125000001439 semicarbazido group Chemical group [H]N([H])C(=O)N([H])N([H])* 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000006248 tosyl amino group Chemical group [H]N(*)S(=O)(=O)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH411282A CH641189A5 (en) | 1977-09-06 | 1982-07-06 | Mono- and diethers of papulacandins A and B |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU75760A LU75760A1 (en, 2012) | 1976-09-09 | 1976-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH636886A5 true CH636886A5 (de) | 1983-06-30 |
Family
ID=19728348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1085377A CH636886A5 (de) | 1976-09-09 | 1977-09-06 | Verfahren zur herstellung von antibiotisch wirksamen, ungesaettigten oder substituierten methylaethern. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4251517A (en, 2012) |
| AT (1) | AT355207B (en, 2012) |
| AU (1) | AU519162B2 (en, 2012) |
| BE (1) | BE858492A (en, 2012) |
| CA (1) | CA1114813A (en, 2012) |
| CH (1) | CH636886A5 (en, 2012) |
| DE (1) | DE2739974A1 (en, 2012) |
| DK (1) | DK399877A (en, 2012) |
| ES (1) | ES462251A1 (en, 2012) |
| FR (1) | FR2364226A1 (en, 2012) |
| GB (1) | GB1590811A (en, 2012) |
| LU (1) | LU75760A1 (en, 2012) |
| NL (1) | NL7709952A (en, 2012) |
| SE (1) | SE7710088L (en, 2012) |
| ZA (1) | ZA775417B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054514A1 (de) * | 1980-12-16 | 1982-06-23 | Ciba-Geigy Ag | Neue antibiotisch wirksame Aminopapulacandin-Derivate |
| US5091413A (en) * | 1990-02-13 | 1992-02-25 | Merck & Co., Inc. | Antibiotic agent |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2218569A (en) * | 1939-09-13 | 1940-10-22 | Dow Chemical Co | Glycosides of pentose ethers |
| US2235786A (en) * | 1939-09-13 | 1941-03-18 | Dow Chemical Co | Pentoside ethers |
| US2235785A (en) * | 1939-09-13 | 1941-03-18 | Dow Chemical Co | Sorbitol ethers |
| US2258171A (en) * | 1940-08-14 | 1941-10-07 | Dow Chemical Co | Monosaccharose ethers from polysaccharide ethers |
| CH464957A (de) * | 1965-12-14 | 1968-11-15 | Sandoz Ag | Verfahren zur Herstellung eines neuen Glucosids |
| CH539032A (de) * | 1969-07-03 | 1973-07-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Hexafuranoseverbindungen |
| US3935184A (en) * | 1972-02-22 | 1976-01-27 | Syntex (U.S.A.) Inc. | Synthetic polyoxin type nucleosides |
| US4017608A (en) * | 1973-12-14 | 1977-04-12 | Strategic Medical Research Corporation | Therapeutic composition and method of therapeutically treating warm blooded animals therewith |
| DE2609611A1 (de) * | 1975-03-13 | 1976-09-23 | Ciba Geigy Ag | Verfahren zur herstellung eines neuen antibiotikums |
-
1976
- 1976-09-09 LU LU75760A patent/LU75760A1/xx unknown
-
1977
- 1977-09-06 DE DE19772739974 patent/DE2739974A1/de not_active Withdrawn
- 1977-09-06 CH CH1085377A patent/CH636886A5/de not_active IP Right Cessation
- 1977-09-07 FR FR7727105A patent/FR2364226A1/fr active Granted
- 1977-09-07 AU AU28623/77A patent/AU519162B2/en not_active Expired
- 1977-09-07 CA CA286,187A patent/CA1114813A/en not_active Expired
- 1977-09-08 AT AT646277A patent/AT355207B/de not_active IP Right Cessation
- 1977-09-08 BE BE180741A patent/BE858492A/xx not_active IP Right Cessation
- 1977-09-08 SE SE7710088A patent/SE7710088L/xx not_active Application Discontinuation
- 1977-09-08 DK DK399877A patent/DK399877A/da not_active Application Discontinuation
- 1977-09-08 GB GB37522/77A patent/GB1590811A/en not_active Expired
- 1977-09-08 ZA ZA00775417A patent/ZA775417B/xx unknown
- 1977-09-09 NL NL7709952A patent/NL7709952A/xx not_active Application Discontinuation
- 1977-09-09 ES ES77462251A patent/ES462251A1/es not_active Expired
-
1979
- 1979-06-27 US US06/052,362 patent/US4251517A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2364226B1 (en, 2012) | 1982-10-29 |
| FR2364226A1 (fr) | 1978-04-07 |
| ZA775417B (en) | 1978-07-26 |
| DK399877A (da) | 1978-03-10 |
| BE858492A (fr) | 1978-03-08 |
| AU2862377A (en) | 1979-03-15 |
| US4251517A (en) | 1981-02-17 |
| LU75760A1 (en, 2012) | 1978-04-27 |
| DE2739974A1 (de) | 1978-03-16 |
| NL7709952A (nl) | 1978-03-13 |
| AU519162B2 (en) | 1981-11-12 |
| AT355207B (de) | 1980-02-25 |
| CA1114813A (en) | 1981-12-22 |
| ATA646277A (de) | 1979-07-15 |
| ES462251A1 (es) | 1978-12-01 |
| SE7710088L (sv) | 1978-03-10 |
| GB1590811A (en) | 1981-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |