NO121047B - - Google Patents
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- Publication number
- NO121047B NO121047B NO17002467A NO17002467A NO121047B NO 121047 B NO121047 B NO 121047B NO 17002467 A NO17002467 A NO 17002467A NO 17002467 A NO17002467 A NO 17002467A NO 121047 B NO121047 B NO 121047B
- Authority
- NO
- Norway
- Prior art keywords
- ether
- general formula
- chlorine
- fluorine
- acetic acid
- Prior art date
Links
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- SHYRNAJCPIECFE-UHFFFAOYSA-N 1-(2-anilinophenyl)ethanone Chemical class CC(=O)C1=CC=CC=C1NC1=CC=CC=C1 SHYRNAJCPIECFE-UHFFFAOYSA-N 0.000 description 2
- WCSGSHPFLOUHDV-UHFFFAOYSA-N 1-[2-(2,6-dichloroanilino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl WCSGSHPFLOUHDV-UHFFFAOYSA-N 0.000 description 2
- LZHUTAUPAKOTFY-UHFFFAOYSA-N CCO[Mg].CCOC(=O)CC(=O)OCC Chemical compound CCO[Mg].CCOC(=O)CC(=O)OCC LZHUTAUPAKOTFY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- -1 [2-(2,6 -dichloro-m-toluidino)-5-chlorophenyl]-acetic acid Chemical compound 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001741 anti-phlogistic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QNBAUJSVBGIPMZ-UHFFFAOYSA-N 1-[2-(2,6-dimethylanilino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1NC1=C(C)C=CC=C1C QNBAUJSVBGIPMZ-UHFFFAOYSA-N 0.000 description 1
- MJBVSNAREWNIBQ-UHFFFAOYSA-N 1-[2-(3-chloro-2-methylanilino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1NC1=CC=CC(Cl)=C1C MJBVSNAREWNIBQ-UHFFFAOYSA-N 0.000 description 1
- CQWSKOHCXHLFHZ-UHFFFAOYSA-N 2-(2,6-dichloroanilino)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl CQWSKOHCXHLFHZ-UHFFFAOYSA-N 0.000 description 1
- GZRAEWKMFPWXNW-UHFFFAOYSA-N 2-[2-(2,6-dichloro-3-methylanilino)phenyl]acetic acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)CC(O)=O)=C1Cl GZRAEWKMFPWXNW-UHFFFAOYSA-N 0.000 description 1
- VGSBGWCOTSSGQY-UHFFFAOYSA-N 2-[2-(2,6-diethylanilino)phenyl]acetic acid Chemical compound CCC1=CC=CC(CC)=C1NC1=CC=CC=C1CC(O)=O VGSBGWCOTSSGQY-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- LJPIGDQQWFXJBF-UHFFFAOYSA-N diethyl 2-(2-anilinobenzoyl)propanedioate Chemical class C(C)OC(C(C(=O)OCC)C(C=1C(NC2=CC=CC=C2)=CC=CC=1)=O)=O LJPIGDQQWFXJBF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (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 Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1451766A CH470349A (de) | 1966-10-07 | 1966-10-07 | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121047B true NO121047B (fi) | 1971-01-11 |
Family
ID=4401487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO17002467A NO121047B (fi) | 1966-10-07 | 1967-10-06 |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT273935B (fi) |
| BE (1) | BE704820A (fi) |
| CH (1) | CH470349A (fi) |
| DK (1) | DK120243B (fi) |
| ES (1) | ES345831A1 (fi) |
| FI (1) | FI47880C (fi) |
| GB (1) | GB1183968A (fi) |
| GR (1) | GR37760B (fi) |
| NL (1) | NL6713629A (fi) |
| NO (1) | NO121047B (fi) |
| SE (1) | SE345997B (fi) |
| YU (1) | YU32369B (fi) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT370721B (de) * | 1981-02-24 | 1983-04-25 | Ciba Geigy Ag | Verfahren zur herstellung von neuen salzen der 2- (2,6-dichloranilino)-phenylessigsaeure, der |
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
-
1966
- 1966-10-07 CH CH1451766A patent/CH470349A/de not_active IP Right Cessation
-
1967
- 1967-10-04 FI FI265567A patent/FI47880C/fi active
- 1967-10-06 GR GR670137760A patent/GR37760B/el unknown
- 1967-10-06 GB GB4572467A patent/GB1183968A/en not_active Expired
- 1967-10-06 YU YU194267A patent/YU32369B/xx unknown
- 1967-10-06 SE SE1371067A patent/SE345997B/xx unknown
- 1967-10-06 AT AT910467A patent/AT273935B/de active
- 1967-10-06 NL NL6713629A patent/NL6713629A/xx unknown
- 1967-10-06 DK DK497867A patent/DK120243B/da not_active IP Right Cessation
- 1967-10-06 NO NO17002467A patent/NO121047B/no unknown
- 1967-10-06 BE BE704820D patent/BE704820A/xx unknown
- 1967-10-06 ES ES345831A patent/ES345831A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH470349A (de) | 1969-03-31 |
| SE345997B (fi) | 1972-06-19 |
| YU194267A (en) | 1974-04-30 |
| FI47880C (fi) | 1974-04-10 |
| YU32369B (en) | 1974-10-31 |
| AT273935B (de) | 1969-08-25 |
| GR37760B (el) | 1969-07-12 |
| GB1183968A (en) | 1970-03-11 |
| ES345831A1 (es) | 1968-11-16 |
| DK120243B (da) | 1971-05-03 |
| FI47880B (fi) | 1974-01-02 |
| NL6713629A (fi) | 1968-04-08 |
| BE704820A (fi) | 1968-04-08 |
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