NO121502B - - Google Patents
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- Publication number
- NO121502B NO121502B NO1756/68A NO175668A NO121502B NO 121502 B NO121502 B NO 121502B NO 1756/68 A NO1756/68 A NO 1756/68A NO 175668 A NO175668 A NO 175668A NO 121502 B NO121502 B NO 121502B
- Authority
- NO
- Norway
- Prior art keywords
- diethyl
- formula
- sodium hydride
- equimolecular
- mixture
- Prior art date
Links
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 claims description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- RBCXEDQEZDUMHD-UHFFFAOYSA-N 2-fluoropropanedioic acid Chemical class OC(=O)C(F)C(O)=O RBCXEDQEZDUMHD-UHFFFAOYSA-N 0.000 claims description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000005662 Paraffin oil Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- -1 diethyl-α-(p-ethoxyphenyl)-α-fluoromalonate Chemical compound 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- PTJNLAJKMMXRNQ-UHFFFAOYSA-N diethyl 2-dibenzofuran-2-ylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)C1=CC2=C(OC3=C2C=CC=C3)C=C1)=O PTJNLAJKMMXRNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZPLCXHWYPWVJDL-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(O)=CC=C1CC1NC(=O)OC1 ZPLCXHWYPWVJDL-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 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 1
- 208000012659 Joint disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- LQSBAEXJSFLVHM-UHFFFAOYSA-N diethyl 2-(4-ethoxyphenyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=C(OCC)C=C1 LQSBAEXJSFLVHM-UHFFFAOYSA-N 0.000 description 1
- KZWVNVPYBUGYTA-UHFFFAOYSA-N ethyl 2-(4-ethoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(OCC)C=C1 KZWVNVPYBUGYTA-UHFFFAOYSA-N 0.000 description 1
- DOCCDOCIYYDLGJ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C=C1 DOCCDOCIYYDLGJ-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22258/67A GB1175996A (en) | 1967-05-12 | 1967-05-12 | Diethyl-alpha-(2-Dibenzofuranyl)malonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121502B true NO121502B (nl) | 1971-03-08 |
Family
ID=10176453
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1742/68A NO121344B (nl) | 1967-05-12 | 1968-05-04 | |
| NO1756/68A NO121502B (nl) | 1967-05-12 | 1968-05-06 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1742/68A NO121344B (nl) | 1967-05-12 | 1968-05-04 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3567742A (nl) |
| AT (1) | AT277988B (nl) |
| BE (2) | BE714816A (nl) |
| CH (2) | CH484034A (nl) |
| DE (2) | DE1768371B2 (nl) |
| DK (2) | DK122322B (nl) |
| ES (2) | ES353802A1 (nl) |
| FI (3) | FI47662C (nl) |
| FR (4) | FR1583848A (nl) |
| GB (1) | GB1175996A (nl) |
| IL (2) | IL29838A (nl) |
| LU (2) | LU56044A1 (nl) |
| NL (3) | NL149171B (nl) |
| NO (2) | NO121344B (nl) |
| SE (2) | SE353313B (nl) |
| YU (2) | YU32183B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1217689A (en) * | 1967-08-14 | 1970-12-31 | Guppo Lepetit S P A | Ethyl esters of fluro-acetic acids |
| DE2223391C3 (de) * | 1972-05-13 | 1982-02-11 | Merck Patent Gmbh, 6100 Darmstadt | Dibenzofuranderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen enthaltend diese Verbindungen |
| NL7305520A (nl) * | 1972-05-13 | 1973-11-15 | ||
| US3928602A (en) * | 1972-11-01 | 1975-12-23 | Astra Laekemedel Ab | Substituted phenoxymalonic acids, esters thereof and hypolipaemic agents containing the same for lowering lipid levels |
-
1967
- 1967-05-12 GB GB22258/67A patent/GB1175996A/en not_active Expired
-
1968
- 1968-04-16 IL IL29838A patent/IL29838A/en unknown
- 1968-04-16 IL IL29837A patent/IL29837A/xx unknown
- 1968-04-23 CH CH597268A patent/CH484034A/fr not_active IP Right Cessation
- 1968-04-23 CH CH597168A patent/CH483420A/fr not_active IP Right Cessation
- 1968-04-25 NL NL686805923A patent/NL149171B/nl unknown
- 1968-04-25 NL NL6805924A patent/NL6805924A/xx unknown
- 1968-05-02 DK DK202368AA patent/DK122322B/da unknown
- 1968-05-03 US US726557A patent/US3567742A/en not_active Expired - Lifetime
- 1968-05-04 NO NO1742/68A patent/NO121344B/no unknown
- 1968-05-06 NO NO1756/68A patent/NO121502B/no unknown
- 1968-05-06 FI FI681267A patent/FI47662C/fi active
- 1968-05-06 FI FI681268A patent/FI48576C/fi active
- 1968-05-06 FI FI01268/68A patent/FI48576B/fi active
- 1968-05-07 DK DK209868A patent/DK133093C/da active
- 1968-05-07 DE DE19681768371 patent/DE1768371B2/de active Granted
- 1968-05-07 DE DE19681768370 patent/DE1768370B1/de not_active Withdrawn
- 1968-05-08 BE BE714816D patent/BE714816A/xx unknown
- 1968-05-08 BE BE714815D patent/BE714815A/xx unknown
- 1968-05-09 LU LU56044A patent/LU56044A1/xx unknown
- 1968-05-09 LU LU56045A patent/LU56045A1/xx unknown
- 1968-05-09 FR FR1583848D patent/FR1583848A/fr not_active Expired
- 1968-05-10 YU YU1108/68A patent/YU32183B/xx unknown
- 1968-05-10 FR FR1583853D patent/FR1583853A/fr not_active Expired
- 1968-05-10 AT AT455068A patent/AT277988B/de not_active IP Right Cessation
- 1968-05-10 SE SE06364/68A patent/SE353313B/xx unknown
- 1968-05-10 SE SE06363/68A patent/SE331100B/xx unknown
- 1968-05-10 YU YU1109/68A patent/YU31950B/xx unknown
- 1968-05-11 ES ES353802A patent/ES353802A1/es not_active Expired
- 1968-05-11 ES ES353801A patent/ES353801A1/es not_active Expired
- 1968-07-25 FR FR160601A patent/FR8082M/fr not_active Expired
- 1968-08-08 FR FR162347A patent/FR7708M/fr not_active Expired
-
1971
- 1971-03-12 NL NL7103372A patent/NL7103372A/xx unknown
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