DE3636125A1 - Verfahren zur herstellung von diethylenglykolestern - Google Patents
Verfahren zur herstellung von diethylenglykolesternInfo
- Publication number
- DE3636125A1 DE3636125A1 DE19863636125 DE3636125A DE3636125A1 DE 3636125 A1 DE3636125 A1 DE 3636125A1 DE 19863636125 DE19863636125 DE 19863636125 DE 3636125 A DE3636125 A DE 3636125A DE 3636125 A1 DE3636125 A1 DE 3636125A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- benzene
- acid
- hydroxyethoxy
- dichlorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 17
- -1 diethylene glycol ester Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- MRPZLXMWCIWOGP-UHFFFAOYSA-N 2,3-dimethyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1C MRPZLXMWCIWOGP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 claims description 2
- WJCRAVDPIMWFPG-UHFFFAOYSA-N n-phenyl-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NC=2C=CC=CC=2)=C1 WJCRAVDPIMWFPG-UHFFFAOYSA-N 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- SLPAPGNFCSVQKP-UHFFFAOYSA-N 2,6-dichloro-3-methyl-n-phenylaniline Chemical compound CC1=CC=C(Cl)C(NC=2C=CC=CC=2)=C1Cl SLPAPGNFCSVQKP-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- HDUUZPLYVVQTKN-UHFFFAOYSA-N 2,6-dichloro-n-phenylaniline Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 HDUUZPLYVVQTKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
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 |
|---|---|
| DE3636125A1 true DE3636125A1 (de) | 1987-04-30 |
Family
ID=8490031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863636125 Ceased DE3636125A1 (de) | 1985-10-25 | 1986-10-23 | Verfahren zur herstellung von diethylenglykolestern |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0336147A3 (de) * | 1988-03-31 | 1991-03-20 | Merckle GmbH | Diethylenglykolmonoester, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9217066B2 (en) | 2008-03-31 | 2015-12-22 | Ford Global Technologies, Llc | Structural polymer insert and method of making the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834167A1 (de) * | 1978-08-04 | 1980-02-21 | Troponwerke Gmbh & Co Kg | Verfahren zur herstellung von 2-(2-hydroxyaethoxy)aethyl-n-( alpha , alpha , alpha -trifluor-m-tolyl)anthranilat |
| EP0112130A1 (en) * | 1982-12-09 | 1984-06-27 | Teva Pharmaceutical Industries Limited | Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids, their preparation and use |
| 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 |
Family Cites Families (7)
| 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 |
| 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 |
| 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 |
| DE2926472A1 (de) * | 1979-06-30 | 1981-01-15 | Thomae Gmbh Dr K | Neue benzoylderivate, deren herstellung und deren verwendung als arzneimittel |
| DE3476550D1 (en) * | 1983-07-21 | 1989-03-09 | Troponwerke Gmbh & Co Kg | Thermoplastics containing antiphlogistics |
| US4694105A (en) * | 1983-12-20 | 1987-09-15 | Ciba-Geigy Corporation | Herbicidal alkoxyamino- and polyalkoxyaminodiphenyl ethers |
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834167A1 (de) * | 1978-08-04 | 1980-02-21 | Troponwerke Gmbh & Co Kg | Verfahren zur herstellung von 2-(2-hydroxyaethoxy)aethyl-n-( alpha , alpha , alpha -trifluor-m-tolyl)anthranilat |
| EP0112130A1 (en) * | 1982-12-09 | 1984-06-27 | Teva Pharmaceutical Industries Limited | Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids, their preparation and use |
| 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 |
Non-Patent Citations (2)
| Title |
|---|
| Helv.Chim.Acta, Bd. 36, 1953, S. 1109-1115 * |
| HOLLEMANN-WIBERG: Lehrbuch der Anorganischen Chemie, Verlag Walter de Gruyter, Berlin, New York 1985, S. 507 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0336147A3 (de) * | 1988-03-31 | 1991-03-20 | Merckle GmbH | Diethylenglykolmonoester, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8605220A1 (es) | 1986-03-16 |
| IT8621774A0 (it) | 1986-09-19 |
| IT8621774A1 (it) | 1988-03-19 |
| GB2182041A (en) | 1987-05-07 |
| FR2589151B1 (fr) | 1990-05-18 |
| BE905666A (fr) | 1987-02-16 |
| GB2182041B (en) | 1989-09-20 |
| CH676238A5 (enrdf_load_stackoverflow) | 1990-12-28 |
| IT1197255B (it) | 1988-11-30 |
| GB8625481D0 (en) | 1986-11-26 |
| JPS62106064A (ja) | 1987-05-16 |
| ES548226A0 (es) | 1986-03-16 |
| PT81505A (en) | 1985-12-01 |
| PT81505B (pt) | 1987-11-11 |
| FR2589151A1 (fr) | 1987-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8181 | Inventor (new situation) |
Free format text: ORJALES VENERO, AURELIO MOSQUERA PESTANA, RAMON, LEJONA, VIZCAYA, ES |
|
| 8128 | New person/name/address of the agent |
Representative=s name: BERENDT, T., DIPL.-CHEM. DR. LEYH, H., DIPL.-ING. |
|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |