CH676238A5 - - Google Patents
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- Publication number
- CH676238A5 CH676238A5 CH3810/86A CH381086A CH676238A5 CH 676238 A5 CH676238 A5 CH 676238A5 CH 3810/86 A CH3810/86 A CH 3810/86A CH 381086 A CH381086 A CH 381086A CH 676238 A5 CH676238 A5 CH 676238A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxyethoxy
- ethyl
- acid
- diethylene glycol
- dichlorophenylamino
- Prior art date
Links
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- -1 diethylene glycol ester Chemical class 0.000 claims description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- KLLYOVXJTSPZHM-UHFFFAOYSA-N (2,6-dichloroanilino) 2-phenylacetate Chemical compound ClC1=CC=CC(Cl)=C1NOC(=O)CC1=CC=CC=C1 KLLYOVXJTSPZHM-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 150000003385 sodium Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES548226A ES8605220A1 (es) | 1985-10-25 | 1985-10-25 | Procedimiento de preparacion de esteres del dietilenglicol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH676238A5 true CH676238A5 (enrdf_load_stackoverflow) | 1990-12-28 |
Family
ID=8490031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3810/86A CH676238A5 (enrdf_load_stackoverflow) | 1985-10-25 | 1986-10-22 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS62106064A (enrdf_load_stackoverflow) |
| BE (1) | BE905666A (enrdf_load_stackoverflow) |
| CH (1) | CH676238A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3636125A1 (enrdf_load_stackoverflow) |
| ES (1) | ES8605220A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2589151B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2182041B (enrdf_load_stackoverflow) |
| IT (1) | IT1197255B (enrdf_load_stackoverflow) |
| PT (1) | PT81505B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3811118C1 (enrdf_load_stackoverflow) * | 1988-03-31 | 1989-10-12 | Merckle Gmbh, 7902 Blaubeuren, De | |
| US9217066B2 (en) | 2008-03-31 | 2015-12-22 | Ford Global Technologies, Llc | Structural polymer insert and method of making the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1939112C3 (de) * | 1969-08-01 | 1975-03-06 | Troponwerke Dinklage & Co, 5000 Koeln | Ester der N-(3-Trifluormethylphenyl) -anthranilsäure, Verfahren zu ihrer Herstellung und pharmakologisch wirksame Zubereitungen derselben |
| DE2735569A1 (de) * | 1977-08-06 | 1979-02-15 | Troponwerke Gmbh & Co Kg | Verfahren zur herstellung von n-(alpha,alpha,alpha-trifluor-m-tolyl) anthranilsaeure-2-(2-hydroxyaethoxy)aethylester |
| DE2834168C2 (de) * | 1978-08-04 | 1984-02-09 | Troponwerke GmbH & Co KG, 5000 Köln | Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-(α,α,α-trifluor-m-tolyl)anthranilat |
| DE2834167C2 (de) * | 1978-08-04 | 1984-01-26 | Troponwerke GmbH & Co KG, 5000 Köln | Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-(α,α,α-trifluor-m-tolyl)anthranilat |
| DE2834169C2 (de) * | 1978-08-04 | 1984-02-09 | Troponwerke GmbH & Co KG, 5000 Köln | Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-( alpha , alpha , alpha -trifluor-m-tolyl)anthranilat |
| DE2926472A1 (de) * | 1979-06-30 | 1981-01-15 | Thomae Gmbh Dr K | Neue benzoylderivate, deren herstellung und deren verwendung als arzneimittel |
| IL67445A (en) * | 1982-12-09 | 1985-11-29 | Teva Pharma | Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids |
| ATE40561T1 (de) * | 1983-07-21 | 1989-02-15 | Troponwerke Gmbh & Co Kg | Antiphlogistika enthaltende thermoplastische kunststoffe. |
| US4694105A (en) * | 1983-12-20 | 1987-09-15 | Ciba-Geigy Corporation | Herbicidal alkoxyamino- and polyalkoxyaminodiphenyl ethers |
| DE3407507A1 (de) * | 1984-03-01 | 1985-09-05 | A. Nattermann & Cie GmbH, 5000 Köln | Neue o-(2,6-dichloranilino)-phenylessigsaeureester, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
-
1985
- 1985-10-25 ES ES548226A patent/ES8605220A1/es not_active Expired
- 1985-11-15 PT PT81505A patent/PT81505B/pt not_active IP Right Cessation
-
1986
- 1986-09-19 IT IT21774/86A patent/IT1197255B/it active
- 1986-10-22 CH CH3810/86A patent/CH676238A5/de not_active IP Right Cessation
- 1986-10-23 DE DE19863636125 patent/DE3636125A1/de not_active Ceased
- 1986-10-24 GB GB8625481A patent/GB2182041B/en not_active Expired
- 1986-10-24 JP JP61252159A patent/JPS62106064A/ja active Pending
- 1986-10-27 BE BE0/217337A patent/BE905666A/fr not_active IP Right Cessation
- 1986-10-27 FR FR868614922A patent/FR2589151B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES8605220A1 (es) | 1986-03-16 |
| FR2589151B1 (fr) | 1990-05-18 |
| PT81505A (en) | 1985-12-01 |
| ES548226A0 (es) | 1986-03-16 |
| FR2589151A1 (fr) | 1987-04-30 |
| PT81505B (pt) | 1987-11-11 |
| BE905666A (fr) | 1987-02-16 |
| DE3636125A1 (de) | 1987-04-30 |
| JPS62106064A (ja) | 1987-05-16 |
| IT1197255B (it) | 1988-11-30 |
| IT8621774A0 (it) | 1986-09-19 |
| GB2182041A (en) | 1987-05-07 |
| GB8625481D0 (en) | 1986-11-26 |
| IT8621774A1 (it) | 1988-03-19 |
| GB2182041B (en) | 1989-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |