NO115582B - - Google Patents
Download PDFInfo
- Publication number
- NO115582B NO115582B NO160262A NO16026264A NO115582B NO 115582 B NO115582 B NO 115582B NO 160262 A NO160262 A NO 160262A NO 16026264 A NO16026264 A NO 16026264A NO 115582 B NO115582 B NO 115582B
- Authority
- NO
- Norway
- Prior art keywords
- glucosyl
- lower alkyl
- podophyllic acid
- residue
- methyl ester
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 241000237858 Gastropoda Species 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229930013686 lignan Natural products 0.000 claims description 4
- 150000005692 lignans Chemical class 0.000 claims description 4
- 235000009408 lignans Nutrition 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 glucosyl podophyllic acid methyl ester Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NXVJTGLCCSFGAT-QNDDJFOYSA-N (5r,5ar,8ar,9r)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NXVJTGLCCSFGAT-QNDDJFOYSA-N 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000002927 anti-mitotic effect Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 201000006512 mast cell neoplasm Diseases 0.000 description 2
- 208000006971 mastocytoma Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YVCVYCSAAZQOJI-BTINSWFASA-N 4'-demethylpodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-BTINSWFASA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 241000237369 Helix pomatia Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical group 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 229960001237 podophyllotoxin Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/08—Processes in which the treating agent is applied in powder or granular form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH405463A CH427848A (de) | 1963-03-29 | 1963-03-29 | Verfahren zur Herstellung von neuen Verbindungen aus der Lignan-Reihe |
| CH15364 | 1964-01-07 | ||
| CH121864 | 1964-02-03 | ||
| CH154564 | 1964-02-10 | ||
| CH154464 | 1964-02-10 | ||
| CH154664A CH464955A (de) | 1963-03-29 | 1964-02-10 | Verfahren zur Herstellung von neuen Verbindungen aus der Lignan-Reihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115582B true NO115582B (en, 2012) | 1968-10-28 |
Family
ID=27543575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160262A NO115582B (en, 2012) | 1963-03-29 | 1964-03-25 |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE645854A (en, 2012) |
| CH (2) | CH427848A (en, 2012) |
| DK (1) | DK112245B (en, 2012) |
| FR (1) | FR3671M (en, 2012) |
| GB (1) | GB1053339A (en, 2012) |
| LU (1) | LU45761A1 (en, 2012) |
| NL (1) | NL6403149A (en, 2012) |
| NO (1) | NO115582B (en, 2012) |
| OA (1) | OA01224A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4958010A (en) * | 1988-02-16 | 1990-09-18 | Bristol-Myers Company | Epipodophyllotoxin glucoside lactam derivatives |
| US7941989B2 (en) | 2007-09-04 | 2011-05-17 | Everflash, Llc | Deck flashing trim system |
-
0
- GB GB1053339D patent/GB1053339A/en active Active
-
1963
- 1963-03-29 CH CH405463A patent/CH427848A/de unknown
-
1964
- 1964-02-10 CH CH154664A patent/CH464955A/de unknown
- 1964-03-24 NL NL6403149A patent/NL6403149A/xx unknown
- 1964-03-25 NO NO160262A patent/NO115582B/no unknown
- 1964-03-27 LU LU45761D patent/LU45761A1/xx unknown
- 1964-03-27 BE BE645854D patent/BE645854A/xx unknown
- 1964-06-25 FR FR979635A patent/FR3671M/fr not_active Expired
- 1964-12-31 OA OA51408A patent/OA01224A/xx unknown
-
1965
- 1965-11-05 DK DK570365AA patent/DK112245B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6403149A (en, 2012) | 1964-09-30 |
| DK112245B (da) | 1968-11-25 |
| CH154664A4 (en, 2012) | 1968-12-31 |
| FR3671M (fr) | 1965-11-08 |
| GB1053339A (en, 2012) | |
| OA01224A (fr) | 1969-01-25 |
| LU45761A1 (en, 2012) | 1964-09-27 |
| BE645854A (en, 2012) | 1964-09-28 |
| CH427848A (de) | 1967-01-15 |
| CH464955A (de) | 1968-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1591934A (en) | Cyclosporin derivatives | |
| Hodge et al. | N-Glycosyl derivatives of secondary amines | |
| COXON et al. | Simplified preparation of sophorose (2-O-β-D-glucopyranosyl-D-glucose) | |
| NO115582B (en, 2012) | ||
| GB1339032A (en) | Rabelomycin and processes for its production | |
| NO783545L (no) | Fremgangsmaate til fremstilling av deoksynarasinantibiotisk kompleks | |
| NO143026B (no) | Analogifremgangsmaate ved fremstilling av nye, terapeutisk virksomme halogenderivater | |
| DE2705917C3 (de) | Verfahren zur Herstellung von 3 ß , 16 ß -Dihydroxy-5-androsten- 17-on durch mikrobiologische Hydrolyse | |
| Ginsburg et al. | Factors affecting the competitive formation of oxazolines and dehydroalanines from serine derivatives | |
| US3972884A (en) | D-homo-aza-steroids | |
| US3701787A (en) | Preparation of 5,6-dihydro-5-hydroxy-6-propenyl-2-pyrone by fermentation and derivatives thereof | |
| NO138285B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive lincomycinderivater | |
| US3702854A (en) | Synthesis of 2-phenyl benzofurans | |
| US3901890A (en) | Process for production of diketopiperazine dihydroxamates and intermediates therefor | |
| US3947453A (en) | 24-Oxo-14a-aza-D-homo-cholestadiene derivatives | |
| US2697716A (en) | 17alpha-methyl-17bata-hydroxyandrostane-3,6-dione and process | |
| US6380257B1 (en) | Aromatic di-keto derivatives, processes for their production and their use as a pharmaceutical | |
| US3880895A (en) | Hydroxylation of d-13-alkyl-17{60 -ethynyl-hydroxygon-4-en-3-one and derivatures thereof | |
| US2184167A (en) | Manufacture of dihydrofollicle hormones by fermentative reduction | |
| IL25649A (en) | Estra-5(10),7-diene-3,17-dione and its preparation | |
| US4039547A (en) | 24-Methyl-14a-aza-D-homo-cholest-8(9)-enes | |
| NO140010B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme 6-substituerte 3-karbetoksyhydrazinopyridaziner | |
| Theriault et al. | Microbial conversion of 2, 2-diphenyl-3-(1-pyrrolidino) propionitrile | |
| US2983723A (en) | Isonovobiocin and isomerization thereof | |
| US3264185A (en) | Antibiotic pa 166 and method of preparing |