CA1055939A - Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acid - Google Patents
Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acidInfo
- Publication number
- CA1055939A CA1055939A CA252,259A CA252259A CA1055939A CA 1055939 A CA1055939 A CA 1055939A CA 252259 A CA252259 A CA 252259A CA 1055939 A CA1055939 A CA 1055939A
- Authority
- CA
- Canada
- Prior art keywords
- salt
- sulfonic acid
- butyrate
- phenoxyiso
- chloro
- 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.)
- Expired
Links
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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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 Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Abstract of the Disclosure Amine salts of p-dihydroxybenzene sulfonic acid, of which one or both OH groups are sterified with clofibric acid, are useful as hypolipeniates.
Description
lOS5939 The related U.S. Patent No. 3,876,651, issued April 8, 1975 (Canadian Application 171,287), concerns mono and diesters of 2,5-dihydrobenzene sulfonic acid having one of the following general formulas:
O-R O-H O-R
53'3 ~_503-B ~-- 3 O-H O-R O-R' I II III
wherein R and R' can be the same or different and represent an alkanoyl, arylalkanoyl, aryloxyalkanoyl, aroyl, alkanesulfonyl, arenesulfonyl, alkylarensulfonyl or arylalkanesulfonyl radical, B represents an alkaline metal, alkaline earth metal, ammonia or a substituted or unsubstituted open chained or cyclic amine cation.
The process for preparing these compounds is characterized by the fact that the compound of formula:
O-H
~ SO3.B
O-H
is reacted with a halide or an anhydride of an acid of formula R-H, and possibly an acid of formula R'-H wherein B and R and R' have the meaning given above.
One has now found, after a study of sub-chronic toxicity in the rat, that particular salts of the diester of p-chlorophenoxy-isobutyric acid, falling within the above definition, prepared by the process according to the parent patent, possess remarkable qualities, particularly with respect to tolerance and effectiveness.
-1- ~
This was shown by the anatomo-pathological study of the various organs of the animal, particularly the liver and kidneys.
Acute toxicity in the mouse was determined according to the modified method of Reed and Muench (Reed L.J. and Muench H., Am. J. Hyg., 27, 493, 1938). The hypolipemiating action in the rat was determined by the method with Triton WR-1339 (Friedmann M. and Byers S.O., J. Exptl. Med., 97, 117, 1953), on the follow-ing parameters: cholesterol, method of Liebermann and Burchard, modified by Richterich (Richterich R. and Lauber K., Klin. Wschr., 40, 1952, 1962), total lipids: method of Zollner and Kirsh (Zollner H. and Kirsh K., Z. ges. exp. Med., 135, 545, 1962) and triglycerids, densitometry after plasma extraction according to the method of Folch (Folch J. Lees M. and Sloane-Stanley G.H., J. Biol. Chem., 226, 497, 1957) and separation by thin layer chromatography. Concerning the daily human dosage administered in various pharmaceutical forms, a possible dose is given below.
Example 1 To a solution of 0.8 g of diethylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol is added. Themixture is heated, it is cooled to ambient temperature, then in a refrigerator for 2 hours, it is filtered, the product formed is recrystallized and 4.3 g of the diethylamine salt of the di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained, in the form of white crystals having a melting point of 176C.
Example 2 To a solution of 1.0 g of dipropylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol is added. Themixture is heated and left in a refrigerator for 4 hours, it is iO55939 filtered, the product formed is recrystallized and 6.4 g of the dipropylamine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained, in the form of white crystals having a melting point of 117C.
Example 3 To a solution of 1.3 g of dibutylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol are added. The mixture is heated and left in a refrigerator for 5 hours, it is filtered, the product formed is recrystallized and 4.2 g of the dibutylamine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-: dihydroxybenzenesulfonic acid are obtained in the form of white crystals having a melting point of 116C.
Example 4 To a solution of 0.8 g of morpholine in 20 ml of ethanol,a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol are added. The mixture is heated and left in a refrigerator for 5 hours, it is filtered, the product formed is recrystallized and 5.1 g of the morpholine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained in the form of white crystals having a melting point of 160C.
., ~
,y o o o o o o o o o ,, ., ~ p, ~ ~ N ~`1 0 ~1 U~
r~
0 ~1 .,, a O rl Q) O
O
S~
J, UJ ~1 ~ N
I ~>1 0 >`1 1 ~
O X S~ X O X X
~ O O 0 ~1 0 1 0 0 ~1 ~1 S-l 0 ~1 0 ~1 ~ ~ O
_ I I I _ I I I
I u~ o ul I ~ Sl~u~l O` I` O` --`
.,1 ~ ~1 0 O ~ O O ~r~ O
O ~ ~1 O ~~ 1 0 ~ ~1 ~ rl ~ h Uu~ ~1 U al S~ U ~ Ll U
:.: a) ~ o~ ~ o ~ ~ o u~ ~ o Q ~ F, Q ~1 ~ ~1 ~1 o ~~ o ~ ~1 0 ~ ~ O
~X ~ ~X ~ ~X ~ O X
o a)o o C) ~ o a) ~ o a) ~, N5~ ~, N ~ ~ N ~, ~ N
a P~Q ~ Q
O-R O-H O-R
53'3 ~_503-B ~-- 3 O-H O-R O-R' I II III
wherein R and R' can be the same or different and represent an alkanoyl, arylalkanoyl, aryloxyalkanoyl, aroyl, alkanesulfonyl, arenesulfonyl, alkylarensulfonyl or arylalkanesulfonyl radical, B represents an alkaline metal, alkaline earth metal, ammonia or a substituted or unsubstituted open chained or cyclic amine cation.
The process for preparing these compounds is characterized by the fact that the compound of formula:
O-H
~ SO3.B
O-H
is reacted with a halide or an anhydride of an acid of formula R-H, and possibly an acid of formula R'-H wherein B and R and R' have the meaning given above.
One has now found, after a study of sub-chronic toxicity in the rat, that particular salts of the diester of p-chlorophenoxy-isobutyric acid, falling within the above definition, prepared by the process according to the parent patent, possess remarkable qualities, particularly with respect to tolerance and effectiveness.
-1- ~
This was shown by the anatomo-pathological study of the various organs of the animal, particularly the liver and kidneys.
Acute toxicity in the mouse was determined according to the modified method of Reed and Muench (Reed L.J. and Muench H., Am. J. Hyg., 27, 493, 1938). The hypolipemiating action in the rat was determined by the method with Triton WR-1339 (Friedmann M. and Byers S.O., J. Exptl. Med., 97, 117, 1953), on the follow-ing parameters: cholesterol, method of Liebermann and Burchard, modified by Richterich (Richterich R. and Lauber K., Klin. Wschr., 40, 1952, 1962), total lipids: method of Zollner and Kirsh (Zollner H. and Kirsh K., Z. ges. exp. Med., 135, 545, 1962) and triglycerids, densitometry after plasma extraction according to the method of Folch (Folch J. Lees M. and Sloane-Stanley G.H., J. Biol. Chem., 226, 497, 1957) and separation by thin layer chromatography. Concerning the daily human dosage administered in various pharmaceutical forms, a possible dose is given below.
Example 1 To a solution of 0.8 g of diethylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol is added. Themixture is heated, it is cooled to ambient temperature, then in a refrigerator for 2 hours, it is filtered, the product formed is recrystallized and 4.3 g of the diethylamine salt of the di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained, in the form of white crystals having a melting point of 176C.
Example 2 To a solution of 1.0 g of dipropylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol is added. Themixture is heated and left in a refrigerator for 4 hours, it is iO55939 filtered, the product formed is recrystallized and 6.4 g of the dipropylamine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained, in the form of white crystals having a melting point of 117C.
Example 3 To a solution of 1.3 g of dibutylamine in 20 ml of ethanol, a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol are added. The mixture is heated and left in a refrigerator for 5 hours, it is filtered, the product formed is recrystallized and 4.2 g of the dibutylamine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-: dihydroxybenzenesulfonic acid are obtained in the form of white crystals having a melting point of 116C.
Example 4 To a solution of 0.8 g of morpholine in 20 ml of ethanol,a solution of 6.0 g of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid in 10 ml of ethanol are added. The mixture is heated and left in a refrigerator for 5 hours, it is filtered, the product formed is recrystallized and 5.1 g of the morpholine salt of di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzenesulfonic acid are obtained in the form of white crystals having a melting point of 160C.
., ~
,y o o o o o o o o o ,, ., ~ p, ~ ~ N ~`1 0 ~1 U~
r~
0 ~1 .,, a O rl Q) O
O
S~
J, UJ ~1 ~ N
I ~>1 0 >`1 1 ~
O X S~ X O X X
~ O O 0 ~1 0 1 0 0 ~1 ~1 S-l 0 ~1 0 ~1 ~ ~ O
_ I I I _ I I I
I u~ o ul I ~ Sl~u~l O` I` O` --`
.,1 ~ ~1 0 O ~ O O ~r~ O
O ~ ~1 O ~~ 1 0 ~ ~1 ~ rl ~ h Uu~ ~1 U al S~ U ~ Ll U
:.: a) ~ o~ ~ o ~ ~ o u~ ~ o Q ~ F, Q ~1 ~ ~1 ~1 o ~~ o ~ ~1 0 ~ ~ O
~X ~ ~X ~ ~X ~ O X
o a)o o C) ~ o a) ~ o a) ~, N5~ ~, N ~ ~ N ~, ~ N
a P~Q ~ Q
Claims (20)
1. A process for the preparation of a salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid wherein said salt is selected from the group consisting of diethylamine salt, dipropylamine salt, dibutylamine salt and morpholine salt, said process comprising the step of reacting, with di-O-(p-chlorophenoxyisobutyrate) of 2,5-dihydroxybenzene-sulfonic acid; a basic compound selected from the group consisting of diethylamine, dipropylamine, dibutylamine and morpholine,
2. The process as in claim 1, wherein said process is carried out at an elevated temperature.
3. The process as in claim 1, wherein said process is carried out in ethanol.
4. The process as in claim 1, wherein the basic second reactant is diethylamine; and the product is the diethylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
5. The process as in claim 2, wherein the basic second reactant is diethylamine; and the product is the diethylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
6. The process as in claim 3, wherein the basic second reactant is diethylamine; and the product is the diethylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
7. The process as in claim 1, wherein the basic second reactant is dipropylamine; and the product is the dipropylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
8. The process as in claim 2, wherein the basic second reactant is dipropylamine; and the product is the dipropylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
9. The process as in claim 3, wherein the basic second reactant is dipropylamine; and the product is the dipropylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
10. The process as in claim 1, wherein the basic second reactant is dibutylamine; and the product is the dibutylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
11. The process as in claim 2, wherein the basic second reactant is dibutylamine; and the product is the dibutylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
12. The process as in claim 3, wherein the basic second reactant is dibutylamine; and the product is the dibutylamine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
13. The process as in claim 1, wherein the basic second reactant is morpholine; and the product is the morpholine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
14. The process as in claim 2, wherein the basic second reactant is morpholine; and the product is the morpholine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
15. The process as in claim 3, wherein the basic second reactant is morpholine; and the product is the morpholine salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid.
16. A salt of di-O-(p-chloro-phenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acld wherein said salt is selected from the group consisting of the diethylamine salt, dipropylamine salt, dibutylamine salt and morpholine salt, whenever prepared by the process of claim 1, 2 or 3, or by an obvious chemical equivalent thereof.
17. The diethylamine salt of di-O-(p-chlorophenoxy-isobutyrate) of 2,5-dihydroxybenzene sulfonic acid, whenever prepared by the process of claim 4, 5 or 6, or by an obvious chemical equivalent thereof.
18. The dipropylamine salt of di-O-(p-chlorophenoxy-isobutyrate) of 2,5-dihydroxybenzene sulfonic acid, whenever prepared by the process of claim 7, 8 or 9, or by an obvious chemical equivalent thereof.
19. The dibutylamine salt of di-O-(p-chlorophenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid, whenever prepared by the process of claim 10, 11 or 12, or by an obvious chemical equivalent thereof.
20. The morpholine salt of di-O-(p-chlorophenoxyiso-butyrate) of 2,5-dihydroxybenzene sulfonic acid, whenever prepared by the process of claim 13, 14 or 15, or by an obvious chemical equivalent thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH633275A CH591438A5 (en) | 1975-05-16 | 1975-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055939A true CA1055939A (en) | 1979-06-05 |
Family
ID=4307867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA252,259A Expired CA1055939A (en) | 1975-05-16 | 1976-05-11 | Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acid |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51148011A (en) |
| AU (1) | AU1107276A (en) |
| BE (1) | BE838182R (en) |
| CA (1) | CA1055939A (en) |
| CH (1) | CH591438A5 (en) |
| DD (1) | DD125201A6 (en) |
| DE (1) | DE2618450A1 (en) |
| DK (1) | DK131476A (en) |
| FR (1) | FR2310755A2 (en) |
| GB (1) | GB1500481A (en) |
| NL (1) | NL182050C (en) |
| RO (1) | RO72828A (en) |
| ZA (1) | ZA76689B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH563356A5 (en) * | 1972-05-17 | 1975-06-30 | Esteve Dr Lab Del Sa | |
| CH551956A (en) * | 1972-05-17 | 1974-07-31 | Esteve Lab Del Dr Sa | PROCESS FOR THE PREPARATION OF SULPHONES SALTS DERIVED FROM 2,5-DIHYDROXYBENZENEMONOSULPHONIC AND 2,5DIHYDROXYBENZENEDISULPHONIC ACIDS. |
| AR204506A1 (en) * | 1972-05-17 | 1976-02-12 | Esteve Labor Dr | PROCEDURE FOR THE PREPARATION OF SALTS OF P-DIHYDROXYBENE DISULPHONIC ACIDS |
-
1975
- 1975-05-16 CH CH633275A patent/CH591438A5/xx not_active IP Right Cessation
- 1975-12-20 RO RO7584261A patent/RO72828A/en unknown
-
1976
- 1976-01-20 NL NLAANVRAGE7600527,A patent/NL182050C/en active Search and Examination
- 1976-01-23 FR FR7601920A patent/FR2310755A2/en active Granted
- 1976-01-29 GB GB3629/76A patent/GB1500481A/en not_active Expired
- 1976-02-02 BE BE164018A patent/BE838182R/en not_active IP Right Cessation
- 1976-02-06 ZA ZA760689A patent/ZA76689B/en unknown
- 1976-02-12 AU AU11072/76A patent/AU1107276A/en not_active Expired
- 1976-03-25 DK DK131476A patent/DK131476A/en unknown
- 1976-04-27 DE DE19762618450 patent/DE2618450A1/en active Granted
- 1976-05-11 CA CA252,259A patent/CA1055939A/en not_active Expired
- 1976-05-14 JP JP51054442A patent/JPS51148011A/en active Pending
- 1976-05-14 DD DD192854A patent/DD125201A6/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2310755A2 (en) | 1976-12-10 |
| FR2310755B2 (en) | 1978-11-03 |
| JPS51148011A (en) | 1976-12-18 |
| ZA76689B (en) | 1977-09-28 |
| CH591438A5 (en) | 1977-09-15 |
| AU1107276A (en) | 1977-08-18 |
| DE2618450C2 (en) | 1987-11-12 |
| GB1500481A (en) | 1978-02-08 |
| RO72828A (en) | 1981-05-30 |
| NL7600527A (en) | 1976-11-18 |
| DE2618450A1 (en) | 1976-11-25 |
| DD125201A6 (en) | 1977-04-06 |
| NL182050C (en) | 1988-01-04 |
| DK131476A (en) | 1976-11-17 |
| NL182050B (en) | 1987-08-03 |
| BE838182R (en) | 1976-05-28 |
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