CA1146571A - Process for the preparation of xanthone derivatives - Google Patents
Process for the preparation of xanthone derivativesInfo
- Publication number
- CA1146571A CA1146571A CA000345339A CA345339A CA1146571A CA 1146571 A CA1146571 A CA 1146571A CA 000345339 A CA000345339 A CA 000345339A CA 345339 A CA345339 A CA 345339A CA 1146571 A CA1146571 A CA 1146571A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- effected
- group
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000007964 xanthones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkyl radical Chemical group 0.000 claims description 12
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005751 Copper oxide Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 25
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 230000003266 anti-allergic effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JNPRWSKMJDGYAN-UHFFFAOYSA-N 9-oxoxanthene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 JNPRWSKMJDGYAN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- CQDOCHRASBBSGX-UHFFFAOYSA-N (2-hexyl-4-methylsulfanylphenyl) acetate Chemical compound CCCCCCC1=CC(SC)=CC=C1OC(C)=O CQDOCHRASBBSGX-UHFFFAOYSA-N 0.000 description 2
- WJOKUXWJLDDEOC-UHFFFAOYSA-N (2-hexyl-4-methylsulfanylphenyl) benzoate Chemical compound CCCCCCC1=CC(SC)=CC=C1OC(=O)C1=CC=CC=C1 WJOKUXWJLDDEOC-UHFFFAOYSA-N 0.000 description 2
- NFSCLEXFPXJWDQ-UHFFFAOYSA-N 2-hexyl-4-methylsulfanylphenol Chemical compound CCCCCCC1=CC(SC)=CC=C1O NFSCLEXFPXJWDQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HZDZTPLVTRYOHN-UHFFFAOYSA-N [2-hexyl-4-[s-methyl-n-(4-methylphenyl)sulfonylsulfonimidoyl]phenyl] acetate Chemical compound C1=C(OC(C)=O)C(CCCCCC)=CC(S(C)(=O)=NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 HZDZTPLVTRYOHN-UHFFFAOYSA-N 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- GHPOMFOMBISJGM-UHFFFAOYSA-N dimethyl 2-bromobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1Br GHPOMFOMBISJGM-UHFFFAOYSA-N 0.000 description 1
- ADXCABFZLVXCNW-UHFFFAOYSA-N dimethyl 4-bromobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=C(Br)C(C(=O)OC)=C1 ADXCABFZLVXCNW-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7904649 | 1979-02-09 | ||
| GB7904649 | 1979-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1146571A true CA1146571A (en) | 1983-05-17 |
Family
ID=10503083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345339A Expired CA1146571A (en) | 1979-02-09 | 1980-02-08 | Process for the preparation of xanthone derivatives |
Country Status (15)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL47519A (en) * | 1974-07-09 | 1979-03-12 | Roussel Uclaf | 7-sulphinimidoyl(sulphimidoyl)-xanthone-2-carboxylic acid derivatives, their preparation and pharmaceutical compositions containing them |
| JPS5850225B2 (ja) * | 1976-01-01 | 1983-11-09 | ルセル・ユクラフ | 新規なキサントン類、それらの塩及びエステル並びにこれらの化合物よりなる医薬 |
| SE445346B (sv) * | 1978-03-03 | 1986-06-16 | Roussel Uclaf | Sett att framstella 7-sulfonimidoyl-xanton-2-karboxylsyra-derivat |
-
1979
- 1979-12-27 IL IL59046A patent/IL59046A/xx unknown
-
1980
- 1980-01-08 HU HU808033A patent/HU180552B/hu unknown
- 1980-01-10 ZA ZA00800141A patent/ZA80141B/xx unknown
- 1980-01-30 EP EP80400146A patent/EP0016665B1/fr not_active Expired
- 1980-01-30 DE DE8080400146T patent/DE3060348D1/de not_active Expired
- 1980-01-30 AT AT80400146T patent/ATE967T1/de not_active IP Right Cessation
- 1980-02-07 PT PT70795A patent/PT70795B/pt not_active IP Right Cessation
- 1980-02-08 JP JP1376980A patent/JPS55108867A/ja active Granted
- 1980-02-08 AU AU55350/80A patent/AU531013B2/en not_active Ceased
- 1980-02-08 ES ES488385A patent/ES8102115A1/es not_active Expired
- 1980-02-08 IE IE250/80A patent/IE49389B1/en unknown
- 1980-02-08 GB GB8004291A patent/GB2042540B/en not_active Expired
- 1980-02-08 DK DK54180A patent/DK145948C/da not_active IP Right Cessation
- 1980-02-08 FI FI800392A patent/FI800392A7/fi not_active Application Discontinuation
- 1980-02-08 CA CA000345339A patent/CA1146571A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES488385A0 (es) | 1980-12-16 |
| DK145948B (da) | 1983-04-25 |
| DK54180A (da) | 1980-08-10 |
| EP0016665A1 (fr) | 1980-10-01 |
| ZA80141B (en) | 1981-02-25 |
| PT70795A (fr) | 1980-03-01 |
| ATE967T1 (de) | 1982-05-15 |
| DE3060348D1 (en) | 1982-06-24 |
| JPH0144710B2 (enrdf_load_stackoverflow) | 1989-09-29 |
| JPS55108867A (en) | 1980-08-21 |
| IE49389B1 (en) | 1985-10-02 |
| EP0016665B1 (fr) | 1982-05-05 |
| DK145948C (da) | 1983-09-26 |
| IL59046A0 (en) | 1980-03-31 |
| FI800392A7 (fi) | 1981-08-10 |
| PT70795B (fr) | 1981-06-11 |
| IL59046A (en) | 1985-03-31 |
| HU180552B (en) | 1983-03-28 |
| IE800250L (en) | 1980-08-09 |
| AU531013B2 (en) | 1983-08-04 |
| AU5535080A (en) | 1980-08-14 |
| GB2042540B (en) | 1982-11-24 |
| ES8102115A1 (es) | 1980-12-16 |
| GB2042540A (en) | 1980-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4788282A (en) | Deprotection of allylic esters and ethers | |
| US6013828A (en) | Processes and intermediates useful to make antifolates | |
| US4658055A (en) | Method for manufacture of 7-(2,5-dioxocyclopentyl)heptanoic acid derivative | |
| CA1146571A (en) | Process for the preparation of xanthone derivatives | |
| EP1116719B1 (en) | 3-(1-Hydroxy-pentylidene)-5-nitro-3H-benzofuran-2-one, a process for the preparation thereof and the use thereof | |
| US4225524A (en) | Steroid derivatives and process for preparing the same | |
| KR910003617B1 (ko) | 퀴놀론-및 나프티리돈-카르복실산의 제조방법 | |
| KR890003840B1 (ko) | 8-할로-5, 6-디알콜시퀴나졸린-2, 4-디온의 제조방법 | |
| CA1126282A (en) | Process for the preparation of xanthone derivatives | |
| US5070212A (en) | Intermediates useful for the synthesis of delphinidin chloride | |
| US4079065A (en) | Process for the production of 2H-cyclopenta (b) furan-2-one compounds | |
| PL118827B1 (en) | Method of manufacture of tricyclicdiketone | |
| US5892057A (en) | Preparation of sulfo-N-hydroxysuccinimide salts | |
| US6090168A (en) | Processes and intermediates useful to make antifolates | |
| KR910003630B1 (ko) | 벤조일 아세틱 에스테르 유도체 및 그 제조방법 | |
| JP4148550B2 (ja) | ５−アミノ−１−シクロプロピル−４−オキソキノリン−３−カルボン酸誘導体とその製造方法 | |
| US4242267A (en) | Process for preparing 5-alkyl-7-(S-alkyl-sulfonimidoyl)-xanthone-2-carboxylic acids | |
| US4234491A (en) | Steroid synthesis process using mixed anhydride | |
| CA1066291A (en) | 3-formyl-4-methyl-2,6-dihydroxypyridine and a process for its preparation | |
| CA1254228A (en) | Method of producing the p-chlorophenol ester of p- chlorophenoxyisobutyric acid | |
| JPS5838434B2 (ja) | ２，３，６−トリメチルハイドロキノン−１−ニコチン酸エステルの製造法 | |
| CN111253405A (zh) | 一种比阿培南中间体的制备方法 | |
| KR950001277B1 (ko) | 옥시벤젠 유도체의 제조방법 | |
| CN118852307A (zh) | 一种熊去氧胆酸中间体的制备方法 | |
| JPS60152469A (ja) | シス−ジエステル体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |