NO744537L - - Google Patents
Info
- Publication number
- NO744537L NO744537L NO744537A NO744537A NO744537L NO 744537 L NO744537 L NO 744537L NO 744537 A NO744537 A NO 744537A NO 744537 A NO744537 A NO 744537A NO 744537 L NO744537 L NO 744537L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- preparation
- ethylidene
- product
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 19
- -1 3-phenanthryl Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 229910052801 chlorine Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 20
- 239000000047 product Substances 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 12
- 239000000391 magnesium silicate Substances 0.000 description 12
- 229910052919 magnesium silicate Inorganic materials 0.000 description 12
- 235000019792 magnesium silicate Nutrition 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000709661 Enterovirus Species 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- JKVNPRNAHRHQDD-UHFFFAOYSA-N 1-phenanthren-3-ylethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3C=CC2=C1 JKVNPRNAHRHQDD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- SBMSBQOMJGZBRY-UHFFFAOYSA-N Propioveratrone Chemical compound CCC(=O)C1=CC=C(OC)C(OC)=C1 SBMSBQOMJGZBRY-UHFFFAOYSA-N 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000013553 cell monolayer Substances 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YUTFQTAITWWGFH-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)ethanone Chemical compound C1=CC=C2OC(C(=O)C)=CC2=C1 YUTFQTAITWWGFH-UHFFFAOYSA-N 0.000 description 1
- HUHQPWCDGRZWMH-UHFFFAOYSA-N 1-(3-phenylphenyl)ethanone Chemical group CC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 HUHQPWCDGRZWMH-UHFFFAOYSA-N 0.000 description 1
- VEPUKHYQNXSSKV-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=CC(C(=O)C)=CC=C21 VEPUKHYQNXSSKV-UHFFFAOYSA-N 0.000 description 1
- CRKKDXCKRYPNFM-UHFFFAOYSA-N 1-(5-chloro-1-benzofuran-2-yl)ethanone Chemical compound ClC1=CC=C2OC(C(=O)C)=CC2=C1 CRKKDXCKRYPNFM-UHFFFAOYSA-N 0.000 description 1
- OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 230000002128 anti-rhinoviral effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000007758 minimum essential medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US425423A US3882149A (en) | 1973-12-17 | 1973-12-17 | Substituted benzofuranyl ethylidene carbazic acid esters |
| US00425420A US3856838A (en) | 1973-12-17 | 1973-12-17 | Beta-naphthyl alkylidene carbazic acid esters |
| US00425421A US3855276A (en) | 1973-12-17 | 1973-12-17 | Phenanthryl ethylidene carbazic acid esters |
| US00425422A US3852334A (en) | 1973-12-17 | 1973-12-17 | Substituted carbazic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO744537L true NO744537L (es) | 1975-07-14 |
Family
ID=27503727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO744537A NO744537L (es) | 1973-12-17 | 1974-12-16 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS50116448A (es) |
| AR (1) | AR203665A1 (es) |
| AU (1) | AU7584974A (es) |
| DD (1) | DD118419A5 (es) |
| DE (1) | DE2455684A1 (es) |
| DK (1) | DK648774A (es) |
| FR (1) | FR2254328A1 (es) |
| IL (1) | IL46086A0 (es) |
| NO (1) | NO744537L (es) |
| RO (1) | RO71805A (es) |
| SE (1) | SE7415800L (es) |
-
1974
- 1974-11-20 IL IL46086A patent/IL46086A0/xx unknown
- 1974-11-25 DE DE19742455684 patent/DE2455684A1/de active Pending
- 1974-11-28 AU AU75849/74A patent/AU7584974A/en not_active Expired
- 1974-11-28 AR AR256716A patent/AR203665A1/es active
- 1974-12-12 DK DK648774A patent/DK648774A/da not_active Application Discontinuation
- 1974-12-16 NO NO744537A patent/NO744537L/no unknown
- 1974-12-16 RO RO7480806A patent/RO71805A/ro unknown
- 1974-12-16 SE SE7415800A patent/SE7415800L/xx unknown
- 1974-12-16 DD DD183064A patent/DD118419A5/xx unknown
- 1974-12-17 JP JP49144165A patent/JPS50116448A/ja active Pending
- 1974-12-17 FR FR7441577A patent/FR2254328A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2455684A1 (de) | 1975-06-19 |
| DD118419A5 (es) | 1976-03-05 |
| JPS50116448A (es) | 1975-09-11 |
| FR2254328A1 (en) | 1975-07-11 |
| SE7415800L (es) | 1975-06-18 |
| AR203665A1 (es) | 1975-09-30 |
| IL46086A0 (en) | 1975-03-13 |
| FR2254328B1 (es) | 1977-11-04 |
| AU7584974A (en) | 1976-06-03 |
| DK648774A (es) | 1975-08-25 |
| RO71805A (ro) | 1982-02-26 |
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