NO124535B - - Google Patents
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- Publication number
- NO124535B NO124535B NO2965/68A NO296568A NO124535B NO 124535 B NO124535 B NO 124535B NO 2965/68 A NO2965/68 A NO 2965/68A NO 296568 A NO296568 A NO 296568A NO 124535 B NO124535 B NO 124535B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- solution
- meaning
- reacted
- compound
- Prior art date
Links
- -1 dibenzofuranyl Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical class OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- BDZHKUAKSMWSAJ-UHFFFAOYSA-N 2-chloro-n,n-diethyl-1,1,2-trifluoroethanamine Chemical compound CCN(CC)C(F)(F)C(F)Cl BDZHKUAKSMWSAJ-UHFFFAOYSA-N 0.000 description 2
- RBCXEDQEZDUMHD-UHFFFAOYSA-N 2-fluoropropanedioic acid Chemical class OC(=O)C(F)C(O)=O RBCXEDQEZDUMHD-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CVEADRMKLCECBY-UHFFFAOYSA-N diethyl 2-fluoro-2-[4-(2-methylpropyl)phenyl]propanedioate Chemical compound CCOC(=O)C(F)(C(=O)OCC)C1=CC=C(CC(C)C)C=C1 CVEADRMKLCECBY-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37197/67A GB1217689A (en) | 1967-08-14 | 1967-08-14 | Ethyl esters of fluro-acetic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124535B true NO124535B (fi) | 1972-05-02 |
Family
ID=10394576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2965/68A NO124535B (fi) | 1967-08-14 | 1968-07-27 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3699151A (fi) |
| AT (3) | AT285585B (fi) |
| BE (1) | BE719478A (fi) |
| CH (1) | CH491852A (fi) |
| DE (1) | DE1793134A1 (fi) |
| DK (1) | DK129337B (fi) |
| ES (1) | ES357254A1 (fi) |
| FI (1) | FI48577C (fi) |
| FR (2) | FR1586911A (fi) |
| GB (1) | GB1217689A (fi) |
| IL (1) | IL30393A (fi) |
| LU (1) | LU56661A1 (fi) |
| NL (3) | NL6811321A (fi) |
| NO (1) | NO124535B (fi) |
| SE (1) | SE353315B (fi) |
| YU (1) | YU32185B (fi) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU526817B2 (en) * | 1978-06-21 | 1983-02-03 | Ici Australia Limited | Pesticides |
| EP0068563A3 (en) * | 1981-06-23 | 1983-06-15 | THE PROCTER & GAMBLE COMPANY | Heterocyclic acetic acid compounds and compositions for treating bone diseases |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1964516A (en) * | 1927-10-03 | 1934-06-26 | Selden Co | Production of monocarboxylic acids |
| US1892766A (en) * | 1928-04-03 | 1933-01-03 | Selden Co | Catalytic removal of hydrogen or oxygen containing groups from organic compounds |
| US1925590A (en) * | 1930-12-17 | 1933-09-05 | Selden Co | Production of esters of monocarboxylic acids and their derivatives |
| US2535086A (en) * | 1949-02-08 | 1950-12-26 | George A Breon And Company | Cyclopentyl-(2-methylallyl)-acetic acid |
| NL274986A (fi) * | 1961-02-23 | |||
| US3227736A (en) * | 1962-10-31 | 1966-01-04 | Olin Mathieson | Production of alpha-fluorocarboxylic acids and esters |
| FR1374665A (fr) * | 1963-11-04 | 1964-10-09 | Universal Oil Prod Co | Nouveaux composés phénylacétiques polyalcoyl-substitués et leur procédé de préparation |
| US3557189A (en) * | 1965-04-17 | 1971-01-19 | Bayer Ag | Alpha-chloro-beta-(4-chlorophenyl)-propionic acid methyl ester |
| US3476803A (en) * | 1966-03-16 | 1969-11-04 | Exxon Research Engineering Co | Decarboxylation |
| GB1175996A (en) * | 1967-05-12 | 1970-01-01 | Lepetit Spa | Diethyl-alpha-(2-Dibenzofuranyl)malonate |
-
1967
- 1967-08-14 GB GB37197/67A patent/GB1217689A/en not_active Expired
-
1968
- 1968-07-18 IL IL30393A patent/IL30393A/xx unknown
- 1968-07-27 NO NO2965/68A patent/NO124535B/no unknown
- 1968-08-02 FI FI682195A patent/FI48577C/fi active
- 1968-08-05 US US750009A patent/US3699151A/en not_active Expired - Lifetime
- 1968-08-05 CH CH1169768A patent/CH491852A/fr not_active IP Right Cessation
- 1968-08-07 LU LU56661D patent/LU56661A1/xx unknown
- 1968-08-07 DE DE19681793134 patent/DE1793134A1/de active Granted
- 1968-08-08 NL NL6811321A patent/NL6811321A/xx unknown
- 1968-08-09 DK DK385768AA patent/DK129337B/da unknown
- 1968-08-12 FR FR1586911D patent/FR1586911A/fr not_active Expired
- 1968-08-13 SE SE10900/68A patent/SE353315B/xx unknown
- 1968-08-13 AT AT792668A patent/AT285585B/de active
- 1968-08-13 AT AT1006669A patent/AT285587B/de not_active IP Right Cessation
- 1968-08-13 AT AT1006769A patent/AT285588B/de not_active IP Right Cessation
- 1968-08-14 BE BE719478D patent/BE719478A/xx unknown
- 1968-08-14 YU YU1933/68A patent/YU32185B/xx unknown
- 1968-08-14 ES ES357254A patent/ES357254A1/es not_active Expired
- 1968-11-08 FR FR173000A patent/FR8395M/fr not_active Expired
-
1972
- 1972-02-03 NL NL7201451A patent/NL7201451A/xx unknown
- 1972-02-03 NL NL7201450A patent/NL7201450A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL30393A0 (en) | 1968-09-26 |
| YU32185B (en) | 1974-06-30 |
| LU56661A1 (fi) | 1968-11-14 |
| SE353315B (fi) | 1973-01-29 |
| NL7201451A (fi) | 1972-05-25 |
| FR1586911A (fi) | 1970-03-06 |
| FI48577C (fi) | 1974-11-11 |
| AT285587B (de) | 1970-11-10 |
| FR8395M (fi) | 1971-03-31 |
| IL30393A (en) | 1973-01-30 |
| NL6811321A (fi) | 1969-02-18 |
| ES357254A1 (es) | 1970-03-16 |
| AT285585B (de) | 1970-11-10 |
| DE1793134A1 (de) | 1972-03-09 |
| DK129337C (fi) | 1975-02-17 |
| BE719478A (fi) | 1969-01-16 |
| CH491852A (fr) | 1970-06-15 |
| YU193368A (en) | 1973-12-31 |
| DK129337B (da) | 1974-09-30 |
| NL7201450A (fi) | 1972-05-25 |
| US3699151A (en) | 1972-10-17 |
| FI48577B (fi) | 1974-07-31 |
| GB1217689A (en) | 1970-12-31 |
| AT285588B (de) | 1970-11-10 |
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