HU201541B - Process for production of intermediers of anti-tumour compositions containing epipodophillotoxin or like that - Google Patents
Process for production of intermediers of anti-tumour compositions containing epipodophillotoxin or like that Download PDFInfo
- Publication number
- HU201541B HU201541B HU883526A HU352686A HU201541B HU 201541 B HU201541 B HU 201541B HU 883526 A HU883526 A HU 883526A HU 352686 A HU352686 A HU 352686A HU 201541 B HU201541 B HU 201541B
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- HU
- Hungary
- Prior art keywords
- compounds
- formula
- preparation
- acid addition
- addition salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 title description 9
- 230000000259 anti-tumor effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 methylenedioxy group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-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]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 description 4
- KKUHBVCAEGORJQ-UHFFFAOYSA-N 3-chloro-4,5-dihydro-1,2-oxazole Chemical compound ClC1=NOCC1 KKUHBVCAEGORJQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 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 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
- 229910003446 platinum oxide Inorganic materials 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940034982 antineoplastic agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/722,932 US4644072A (en) | 1985-04-12 | 1985-04-12 | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT47071A HUT47071A (en) | 1989-01-30 |
| HU201541B true HU201541B (en) | 1990-11-28 |
Family
ID=24904037
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU883526A HU201541B (en) | 1985-04-12 | 1986-04-11 | Process for production of intermediers of anti-tumour compositions containing epipodophillotoxin or like that |
| HU863527A HU198063B (en) | 1985-04-12 | 1986-04-11 | Process for producing new intermediates with isoxazole ring of epidophyllotoxin and of analogous antineoplastics |
| HU861538A HU199846B (en) | 1985-04-12 | 1986-04-11 | Process for producing epipodophyllotoxin and analogues thereof |
| HU873238A HU204044B (en) | 1985-04-12 | 1986-04-11 | Process for producing trans-aryltetraloncarboxylic acid derivatives |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU863527A HU198063B (en) | 1985-04-12 | 1986-04-11 | Process for producing new intermediates with isoxazole ring of epidophyllotoxin and of analogous antineoplastics |
| HU861538A HU199846B (en) | 1985-04-12 | 1986-04-11 | Process for producing epipodophyllotoxin and analogues thereof |
| HU873238A HU204044B (en) | 1985-04-12 | 1986-04-11 | Process for producing trans-aryltetraloncarboxylic acid derivatives |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4644072A (enExample) |
| JP (1) | JPS61238758A (enExample) |
| KR (1) | KR900005624B1 (enExample) |
| CN (2) | CN1021822C (enExample) |
| AT (1) | ATA96986A (enExample) |
| AU (6) | AU587021B2 (enExample) |
| BE (1) | BE904587A (enExample) |
| CA (1) | CA1275651C (enExample) |
| CH (2) | CH672635A5 (enExample) |
| CY (1) | CY1599A (enExample) |
| DE (1) | DE3612278A1 (enExample) |
| DK (2) | DK167986A (enExample) |
| EG (1) | EG18077A (enExample) |
| ES (2) | ES8802044A1 (enExample) |
| FI (1) | FI861508A7 (enExample) |
| FR (1) | FR2587335B1 (enExample) |
| GB (1) | GB2176181B (enExample) |
| GR (1) | GR860982B (enExample) |
| HK (1) | HK53391A (enExample) |
| HU (4) | HU201541B (enExample) |
| IE (1) | IE59039B1 (enExample) |
| IL (1) | IL78451A0 (enExample) |
| IT (1) | IT1208593B (enExample) |
| LU (1) | LU86392A1 (enExample) |
| MY (1) | MY101618A (enExample) |
| NL (1) | NL8600938A (enExample) |
| PT (1) | PT82383B (enExample) |
| RU (1) | RU1819265C (enExample) |
| SE (2) | SE468768B (enExample) |
| SG (1) | SG44791G (enExample) |
| SU (1) | SU1547707A3 (enExample) |
| YU (2) | YU44785B (enExample) |
| ZA (1) | ZA862747B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4644072A (en) * | 1985-04-12 | 1987-02-17 | Bristol-Myers Company | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
| US5011948A (en) * | 1985-04-12 | 1991-04-30 | Bristol-Myers Company | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
| US4734512A (en) * | 1985-12-05 | 1988-03-29 | Bristol-Myers Company | Intermediates for the production of podophyllotoxin and related compounds and processes for the preparation and use thereof |
| US5106996A (en) * | 1985-12-05 | 1992-04-21 | Bristol-Myers Company | Process for the preparation of podophyllotoxin |
| US5013851A (en) * | 1985-12-05 | 1991-05-07 | Bristol-Myers Company | Intermediates for the production of podophyllotoxin and related compounds |
| US5880131A (en) * | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5840900A (en) * | 1993-10-20 | 1998-11-24 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5605976A (en) * | 1995-05-15 | 1997-02-25 | Enzon, Inc. | Method of preparing polyalkylene oxide carboxylic acids |
| GB9422947D0 (en) * | 1994-11-14 | 1995-01-04 | Univ Salamanca | Immunosuppressive cyclolignan derivatives |
| EP0757055B1 (de) * | 1995-06-30 | 1999-10-27 | Cerbios-Pharma S.A. | Glykoside, deren zuckerfreie Abbauprodukte und Derivate derselben |
| US6051721A (en) * | 1997-10-02 | 2000-04-18 | The Board Of Regents Of The University Of Nebraska | Ring E-modified analogues of(-)-podophyllotoxin and etoposide and a method for their synthesis |
| HK1049787B (en) | 1999-10-01 | 2014-07-25 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| JOP20190254A1 (ar) | 2017-04-27 | 2019-10-27 | Pharma Mar Sa | مركبات مضادة للأورام |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6613143A (enExample) * | 1965-09-21 | 1967-03-22 | ||
| US3716574A (en) * | 1967-12-01 | 1973-02-13 | Rayonier Inc | Pure crystalline plicatic acid tetrahydrate and the methyl ester thereof |
| US4122092A (en) * | 1977-08-25 | 1978-10-24 | University Of Rochester | Total synthesis of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone |
| US4294763A (en) * | 1980-03-05 | 1981-10-13 | University Of Rochester | Intermediates for the production of picropodophyllin and related compounds and processes for the preparation and use thereof |
| US4391982A (en) * | 1980-03-05 | 1983-07-05 | The University Of Rochester | Intermediates for the production of picropodophyllin and related compounds and processes for the preparation and use thereof |
| AU585936B2 (en) * | 1984-12-28 | 1989-06-29 | Conpharm A.B. | Pharmaceutically active podophyllotoxins |
| NO170760C (no) * | 1985-01-10 | 1992-12-02 | Tanabe Seiyaku Co | Analogifremgangsmaate for fremstilling av terapeutisk aktive nafthalenderivater |
| US4644072A (en) * | 1985-04-12 | 1987-02-17 | Bristol-Myers Company | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
| US4734512A (en) * | 1985-12-05 | 1988-03-29 | Bristol-Myers Company | Intermediates for the production of podophyllotoxin and related compounds and processes for the preparation and use thereof |
-
1985
- 1985-04-12 US US06/722,932 patent/US4644072A/en not_active Expired - Fee Related
-
1986
- 1986-04-04 FR FR868604873A patent/FR2587335B1/fr not_active Expired - Fee Related
- 1986-04-08 IL IL78451A patent/IL78451A0/xx unknown
- 1986-04-09 FI FI861508A patent/FI861508A7/fi not_active Application Discontinuation
- 1986-04-10 ES ES553868A patent/ES8802044A1/es not_active Expired
- 1986-04-10 EG EG197/86A patent/EG18077A/xx active
- 1986-04-11 JP JP61084008A patent/JPS61238758A/ja active Pending
- 1986-04-11 CH CH490/89A patent/CH672635A5/de not_active IP Right Cessation
- 1986-04-11 CN CN86102404A patent/CN1021822C/zh not_active Expired - Fee Related
- 1986-04-11 CH CH1455/86A patent/CH669190A5/de not_active IP Right Cessation
- 1986-04-11 HU HU883526A patent/HU201541B/hu not_active IP Right Cessation
- 1986-04-11 HU HU863527A patent/HU198063B/hu not_active IP Right Cessation
- 1986-04-11 IT IT8620048A patent/IT1208593B/it active
- 1986-04-11 SE SE8601646A patent/SE468768B/sv not_active IP Right Cessation
- 1986-04-11 DK DK167986A patent/DK167986A/da not_active IP Right Cessation
- 1986-04-11 ZA ZA862747A patent/ZA862747B/xx unknown
- 1986-04-11 CA CA000506409A patent/CA1275651C/en not_active Expired - Fee Related
- 1986-04-11 HU HU861538A patent/HU199846B/hu not_active IP Right Cessation
- 1986-04-11 HU HU873238A patent/HU204044B/hu not_active IP Right Cessation
- 1986-04-11 GB GB8608808A patent/GB2176181B/en not_active Expired
- 1986-04-11 IE IE95586A patent/IE59039B1/en not_active IP Right Cessation
- 1986-04-11 KR KR1019860002773A patent/KR900005624B1/ko not_active Expired
- 1986-04-11 LU LU86392A patent/LU86392A1/fr unknown
- 1986-04-11 RU SU864027396A patent/RU1819265C/ru active
- 1986-04-11 AU AU55993/86A patent/AU587021B2/en not_active Ceased
- 1986-04-11 BE BE0/216525A patent/BE904587A/fr not_active IP Right Cessation
- 1986-04-11 DE DE19863612278 patent/DE3612278A1/de not_active Ceased
- 1986-04-14 AT AT0096986A patent/ATA96986A/de not_active Application Discontinuation
- 1986-04-14 NL NL8600938A patent/NL8600938A/nl not_active Application Discontinuation
- 1986-04-14 YU YU594/86A patent/YU44785B/xx unknown
- 1986-04-14 PT PT82383A patent/PT82383B/pt not_active IP Right Cessation
- 1986-04-14 GR GR860982A patent/GR860982B/el unknown
-
1987
- 1987-02-10 SU SU874028952A patent/SU1547707A3/ru active
- 1987-06-16 YU YU112487A patent/YU46212B/sh unknown
- 1987-10-01 MY MYPI87002724A patent/MY101618A/en unknown
- 1987-10-16 ES ES557772A patent/ES8900046A1/es not_active Expired
-
1989
- 1989-06-09 AU AU36287/89A patent/AU607337B2/en not_active Ceased
- 1989-06-09 AU AU36286/89A patent/AU617184B2/en not_active Ceased
- 1989-06-09 AU AU36285/89A patent/AU617183B2/en not_active Ceased
- 1989-06-09 AU AU36288/89A patent/AU617185B2/en not_active Ceased
- 1989-06-09 AU AU36284/89A patent/AU617182B2/en not_active Ceased
-
1991
- 1991-06-15 SG SG44791A patent/SG44791G/en unknown
- 1991-07-11 HK HK533/91A patent/HK53391A/xx unknown
- 1991-10-10 CN CN91109623A patent/CN1059520A/zh active Pending
-
1992
- 1992-04-03 CY CY1599A patent/CY1599A/en unknown
- 1992-08-28 SE SE9202476A patent/SE9202476D0/xx unknown
-
1993
- 1993-10-18 DK DK931171A patent/DK117193D0/da not_active Application Discontinuation
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| HMM4 | Cancellation of final prot. due to non-payment of fee |