BE552628A - - Google Patents
Info
- Publication number
- BE552628A BE552628A BE552628DA BE552628A BE 552628 A BE552628 A BE 552628A BE 552628D A BE552628D A BE 552628DA BE 552628 A BE552628 A BE 552628A
- Authority
- BE
- Belgium
- Prior art keywords
- naphthoquinone
- mol
- ethylene
- aliphatic
- benzene
- Prior art date
Links
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004059 quinone derivatives Chemical class 0.000 claims description 4
- 150000004053 quinones Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 9
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- -1 2-bromo-3-acetyl-ethylamino-1,4-naphthoquinone Chemical compound 0.000 description 1
- VHGFVFVVHXVYTC-UHFFFAOYSA-N 2-chloro-3-(2-oxopropylamino)naphthalene-1,4-dione Chemical compound ClC=1C(C2=CC=CC=C2C(C1NCC(C)=O)=O)=O VHGFVFVVHXVYTC-UHFFFAOYSA-N 0.000 description 1
- IRRTUEIEPNRYCS-UHFFFAOYSA-N 2-methylprop-1-en-1-imine Chemical compound CC(C)=C=N IRRTUEIEPNRYCS-UHFFFAOYSA-N 0.000 description 1
- DWMRIFKCUDJCJD-UHFFFAOYSA-N CC(C(C(C(C(C)=C1C)=O)(NC)Cl)C1=O)=O Chemical compound CC(C(C(C(C(C)=C1C)=O)(NC)Cl)C1=O)=O DWMRIFKCUDJCJD-UHFFFAOYSA-N 0.000 description 1
- LLYRRXZFACBYRL-UHFFFAOYSA-N CC(C(C(C(Cl)=C(C(C)=O)C1=O)=O)=C1NCCCl)=O Chemical compound CC(C(C(C(Cl)=C(C(C)=O)C1=O)=O)=C1NCCCl)=O LLYRRXZFACBYRL-UHFFFAOYSA-N 0.000 description 1
- ITYJYFQGIUIFFL-UHFFFAOYSA-N CC(C(C(C1=CC=CC=C1C1=O)=O)=C1NCCCl)=O Chemical compound CC(C(C(C1=CC=CC=C1C1=O)=O)=C1NCCCl)=O ITYJYFQGIUIFFL-UHFFFAOYSA-N 0.000 description 1
- AFQSDSHPFIXNSS-UHFFFAOYSA-N CNC(C(C(C1=CC=CC=C1)=O)C(C(Cl)=C1C(C2=CC=CC=C2)=O)=O)(C1=O)Cl Chemical compound CNC(C(C(C1=CC=CC=C1)=O)C(C(Cl)=C1C(C2=CC=CC=C2)=O)=O)(C1=O)Cl AFQSDSHPFIXNSS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ADHBVWXFMCERTO-UHFFFAOYSA-N n-(3-chloro-1,4-dioxonaphthalen-2-yl)benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C(Cl)=C1NC(=O)C1=CC=CC=C1 ADHBVWXFMCERTO-UHFFFAOYSA-N 0.000 description 1
- RCWZGXUWCPFMLD-UHFFFAOYSA-N n-(4-benzamido-2,5-dichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)benzamide Chemical compound O=C1C(Cl)=C(NC(=O)C=2C=CC=CC=2)C(=O)C(Cl)=C1NC(=O)C1=CC=CC=C1 RCWZGXUWCPFMLD-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE552628A true BE552628A (d) |
Family
ID=177740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE552628D BE552628A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE552628A (d) |
-
0
- BE BE552628D patent/BE552628A/fr unknown
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