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Echothiopate iodide 1415, washed with water dried Na2SO4 and the solvent removed in vacuum The. residue was salified with the stoichiometric amount of fumaric acid in a. mixture of acetone and ethanol to give 1 3 4 tert butylbenzoyl propyl 4. hydroxypiperidine fumarate 148 g melting point 163 165 C This compound. was converted into the free base and 1 3 4 tert butylbenzoyl propyl 4. hydroxypiperidine was obtained and recrystallized from a mixture of diethyl. ether and petroleum ether boiling point 50 70 C 102 g were obtained yield. 84 melting point 63 65 C, b A mixture of 1 3 tert butylbenzoyl propyl 4 hydroxypiperidine 60 68 g. 0 2 moles and sodium carbonate 42 4 g 0 4 moles in methyl isobutyl. ketone 500 ml was heated to the boiling point and a solution of. diphenylmethyl bromide 49 42 g 0 2 moles in methyl isobutyl ketone 75. ml was slowly added in 1 5 hours The resulting mixture was boiled under. reflux for another 12 hours and then another solution of diphenylmethyl. bromide 24 71 g 0 1 moles in methyl isobutyl ketone 50 ml was added. and the mixture boiled under reflux again for 12 hours Another solution of. diphenylmethyl bromide in the same quantity was added and after refluxing. for 12 additional hours the reaction mixture was cooled washed with water. dried Na2SO4 and the solvent removed in vacuum, The residual oil was treated with the stoichiometric amount of fumaric acid in. ethanol and 4 diphenylmethoxy 1 3 4 tert butylbenzoyl propyl piperidine. fumarate crystallized After recrystallisation from ethanol the pure compound. was obtained 88 g yield 75 melting point 197 198 C. References, Soto Jose M P Noverola Armando V Mauri Jacinto M Spickett Robert US. Patent No 4 550 116 October 29 1985 Assigned to Fordonal S A. ECHOTHIOPATE IODIDE,Therapeutic Function Cholinergic ophthalmic.
Chemical Name 2 Diethoxyphosphinyl thio N N N trimethylethanaminium. Common Name O O Diethyl S dimethylaminoethylthiophosphate methyl. Structural Formula,1416 Echothiopate iodide,Chemical Abstracts Registry No 513 10 0. Trade Name Manufacturer Country Year Introduced,Phospholine Iodide Ayerst US 1959. Phospholine Iodide Promedica France 1966,Echiodide Alcon US 1977. Phospholine Iodide Santen Japan,Phospholine Iodide Ayerst UK. Phospholine Iodide Chinoin Italy,Raw Materials,Dimethylaminoethyl mercaptan hydrochloride.
Diethylchlorophosphate,Methyl iodide,Manufacturing Process. The reaction is carried out in an atmosphere of nitrogen To a solution of 4 60. grams sodium 0 20 mol in 60 cc of methanol is added 14 17 grams. dimethylaminoethyl mercaptan hydro chloride 0 10 mol rinsed in with 10 cc. methanol Solvent is removed at a water pump vacuum while blowing with a. slow stream of nitrogen to 100 C 20 mm To the residue suspended in 150 cc. benzene and cooled in an ice bath is added 17 25 grams. diethylchlorophosphate 0 10 mol in 3 portions at 10 minute intervals After. each addition the temperature increases from about 4 to about 14 C and. then falls The mixture is stirred in an ice bath for one half hour and while. warming to room temperature during 2 hours is washed with 35 and 5 cc. portions of water with two 10 cc portions of saturated brine and is dried over. calcium sulfate and filtered, After removal of solvent by distillation under reduced pressure to 55 C 20. mm the residue is 23 0 grams crude base 95 theory as a pale yellow. liquid A sample of the crude base distills with some decomposition at 105 to. 112 C 0 8 mm, A sample of distilled base in cold isopropanol is treated with excess methyl. iodide left at room temperature overnight diluted with 5 volumes of ethyl. acetate and filtered from the methiodide salt This is purified by crystallization. from mixtures of isopropanol and ethyl acetate filtering hot to remove an. impurity of low solubility The pure methiodide is obtained as a white solid MP. 124 to 124 5 C containing 99 mol percent thiol isomer. References,Merck Index 3481,Kleeman Engel p 345, Fitch H M US Patent 2 911 430 November 3 1959 assigned to Campbell. Pharmaceuticals Inc,Econazole nitrate 1417,ECONAZOLE NITRATE.
Therapeutic Function Antifungal, Chemical Name 1 2 4 Chlorophenyl methoxy 2 2 4 dichlorophenyl. ethyl 1H imidazole nitrate,Common Name,Structural Formula. Chemical Abstracts Registry No 24169 02 6 27220 47 9 Base. Trade Name Manufacturer Country Year Introduced,Pevaryl Cilag Chemie France 1976. Pevaryl Cilag Italy 1978,Ecostatin Fair Labs UK 1978. Pevaryl Cilag Chemie W Germany 1978,Skilar Italchemie Italy 1979.
Paravale Otsuka Japan 1981,Spectazole Ortho US 1983. Epi Pevaryl Cilag W Germany,Gyno Pevaryl Cilag W Germany. Ifenec Italfarmaco Italy,Micoespec Centrum Spain,Micofugal Ion Italy. Micogyn Crosara Italy,Mycopevaryl Cilag,Raw Materials. 2 4 Dichlorophenyl imidazole 1 ethanol,Sodium hydride.
4 Chlorobenzyl chloride,Nitric acid,Manufacturing Process. A suspension of 10 3 parts of 2 4 dichlorophenyl imidazole 1 ethanol and. 2 1 parts of sodium hydride in 50 parts of dry tetrahydrofuran is stirred and. 1418 Ectylurea, refluxed for 2 hours After this reaction time the evolution of hydrogen is. ceased Then there are added successively 60 parts dimethylformamide and 8. parts of p chlorobenzylchloride and stirring and refluxing is continued for. another two hours The tetrahydrofuran is removed at atmospheric pressure. The dimethylformamide solution is poured onto water The product 1 2 4. dichloro p chlorobenzyloxy phenethyl imidazole is extracted with benzene. The extract is washed with water dried filtered and evaporated in vacuo. From the residual oily free base the nitrate salt is prepared in the usual. manner in 2 propanol by treatment with concentrated nitric acid yielding. after recrystallization of the crude solid salt from a mixture of 2 propanol. methanol and diisopropylether 1 2 4 dichloro p, chlorobenzyloxy phenethyl imidazole nitrate MP 162 C. References,Merck Index 3482,Kleeman Engel p 345,PDR p 1309. OCDS Vol 2 p 249 1980,DOT 11 8 310 1975,REM p 1227.
Godefroi E F and Heeres J US Patent 3 717 655 February 20 1973. assigned to Janssen Pharmaceutica NV Belgium,Therapeutic Function Sedative. Chemical Name Z N Aminocarbonyl 2 ethyl 2 butenamide. Common Name Ethylcrotonylurea,Structural Formula,Chemical Abstracts Registry No 95 04 5. Trade Name Manufacturer Country Year Introduced,Nostyn Ames US 1956. Levanil Upjohn US 1959,Cronil Farmigea Italy,Distasol Locatelli Italy. Edetate disodium 1419,Trade Name Manufacturer Country Year Introduced.
Ektyl A C O Sweden,Neuroprocin Minerva Chemie Netherlands. Raw Materials,2 Bromo 2 ethylbutyryl urea carbromal. Silver oxide,Manufacturing Process, 54 g of carbromal 2 bromo 2 ethylbutyryl urea in 600 cc of isopropanol was. stirred and refluxed for 3 hours with 27 8 g of anhydrous silver oxide The. reaction mixture was filtered and the silver residue was extracted with 100 cc. of boiling isopropanol The filtered and dried solids which separated weighed. 22 5 g and melted at 189 C to 190 5 C Concentration of the filtrate yielded. an additional 3 3 g of product which melted at 160 C to 170 C These two. crops were separately obtained as white needles by crystallization from. alcohol and exhibited slight solubility in water The first crop gave 21 7 g of 2. ethyl cis crotonyl urea with a melting point of 191 C to 193 C and the. second crop gave 0 9 g with a melting point of 191 C to 193 C for a total. yield of 42 4 g or 63 of the theoretical,References. Merck Index 3484,OCDS Vol 1 p 221 1977, Faucher O E US Patents 2 854 379 September 30 1958 and 2 931 832.
April 5 1960 both assigned to Miles Laboratories Inc. EDETATE DISODIUM, Therapeutic Function Pharmaceutic aid chelating agent. Chemical Name N N 1 2 Ethanediylbis N carboxymethyl glycine disodium. Common Name EDTA disodium,Structural Formula,1420 Edetate disodium. Chemical Abstracts Registry No 139 33 3,Trade Name Manufacturer Country Year Introduced. Endrate Disodium Bersworth US 1959,Cheladrate PHARMEX US. Diso Tate O Neal Jones US,Idranal Riedel de Hahn W Germany.
Komplexon III Chemische Fabrik Switz,Uni Wash United US. Raw Materials,Ethylene diamine,Sodium cyanide,Formaldehyde. Sodium hydroxide,Manufacturing Process, 10 mols of ethylene diamine as a 30 aqueous solution and 4 mols of solid. caustic soda are placed in a steam heated kettle supplied with an agitator 8. mols of sodium cyanide as a concentrated water solution about 30 are. added and the solution heated to 60 C About a 10 inch vacuum is applied to. bring the liquid to incipient boiling Formaldehyde 7 5 mols of 37 to 40. aqueous solution is slowly added the temperature being held at 60 C and. the solution vigorously stirred Then when the evolution of ammonia has. substantially stopped an additional 8 mols of sodium cyanide followed by 8. mols of formaldehyde are added as before This is continued until 40 mols of. cyanide and 40 mols of formaldehyde have been added Then at the end. about 2 mols more of formaldehyde are added making 42 mols in all to. remove any last traces of cyanide About 8 to 10 hours are required to. complete the reaction The resulting product referred to herein as the crude. reaction product is essentially an aqueous solution of the sodium salt of. ethylene diamine tetracetic acid, To 1 000 g of the crude reaction product are added 264 g of ethylene diamine. tetracetic acid The mixture is preferably heated to incipient boiling to increase. the rate of reaction and then the mixture is allowed to cool and crystallize. The crystals formed are filtered off washed with the smallest possible amount. of ice water and dried to a constant weight which is 452 g A representative. sample of the product so prepared showed upon analysis 13 26 sodium. against a theoretical of 13 70 for the disodium salt The dialkali salt has a. pH of about 5 3 and behaves like a weak acid displacing CO2 from carbonates. and reacting with metals to form hydrogen It is a white crystalline solid. References,Merck Index 3487,PDR p 1826, Bersworth F C US Patent 2 407 645 September 17 1946 assigned to The.
Martin Dennis Co,Edrophonium chloride 1421,EDROPHONIUM CHLORIDE. Therapeutic Function Cholinergic, Chemical Name N Ethyl 3 hydroxy N N dimethylbenzeneaminium chloride. Common Name,Structural Formula,Chemical Abstracts Registry No 116 38 1. Trade Name Manufacturer Country Year Introduced,Tensilon Roche US 1951. Tensilon Roche UK,Antirex Kyorin Japan,Raw Materials.
m Dimethylaminophenol Ethyl iodide,Sodium hydroxide Silver nitrate. Hydrogen chloride,Manufacturing Process, A solution made up of 10 grams of m dimethylaminophenol 50 cc of acetone. and 13 grams of ethyl iodide was heated at 50 C for five hours On addition. of ether to the cooled solution 3 hydroxyphenyl ethyl dimethylammonium. iodide precipitated as an oil which soon crystallized Upon recrystallization. from isopropanol the compound had a MP of 113 to 115 C. A slight excess of a 10 sodium hydroxide solution was added to a solution of. 23 grams of silver nitrate in 300 cc of water The precipitated silver oxide was. washed free of silver ion with distilled water To a suspension of the silver. oxide in 200 cc of water a solution of 25 grams of 3 hydroxyphenyl ethyl. dimethylammonium iodide in 300 cc of water was added The precipitate of. silver iodide was removed by filtration and the filtrate concentrated to a. volume of about 100 cc in vacuo The remainder of the water was removed by. lyophilization 3 hydroxyphenyl ethyl dimethylammonium hydroxide was. obtained as a hygroscopic amorphous solid, A solution of 5 grams of 3 hydroxyphenyl ethyl dimethylammonium. hydroxide in about 200 cc of water was neutralized with dilute hydrochloric. acid On concentration to dry ness in vacuo 3 hydroxyphenyl ethyl. dimethylammonium chloride crystallized The compound was recrystallized. 1422 Efavirenz, from isopropanol MP 162 to 163 C with decomposition. References,Merck Index 3492,Kleeman Engel p 346,PDR pp 1504 2009.
Terrell R C US Patents 3 469 011 September 23 1969 and 3 527 813. September 8 1970 both assigned to Air Reduction Company. Incorporated,Therapeutic Function Antiviral, Chemical Name 2H 3 1 Benzoxazin 2 one 6 chloro 4 cyclopropylethynyl. 1 4 dihydro 4 trifluoromethyl 4S,Common Name Efavirenz. Structural Formula,Chemical Abstracts Registry No 154598 52 4. Trade Name Manufacturer Country Year Introduced,DMP 266 DuPont Merck. Efavirenz Bristol Myers USA,Stocrin Merck Sharp and Netherlands.
Sustiva Bristol Myers USA,Sustiva DuPont,Pharmaceuticals. Efavirenz 1423,Raw Materials,Ethylmagnesium bromide Cyclopropylacetylene. 1 2 Amino 5 chlorophenyl 2 2 2 1 1 Carbonyldiimidazole. trifluoromethylethanone 4 Dimethylaminopyridine,Camphanic acid chloride Triethylamine. Manufacturing Process, 6 Chloro 4 cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H 3 1. benzoxazin 2 one and 6 Chloro 4 cyclopropylethynyl 4 trifluoromethyl. 1 4 dihydro 2H 3 1 benzoxazin 2 one, The above products can be produced in the next steps.
Step A 2 2 Amino 5 chlorophenyl 4 cyclopropyl 1 1 1 trifluoro 3 butyn 2. A solution was prepared from 23 g of cyclopropylacetylene 0 348 mol in. 250 mL of THF by dropwise addition of 116 mL of a 3 0 M solution of. ethylmagnesium bromide in ether 0 348 mol over 1 h This solution was. maintained at 0 C for 1 h then at 40 C for 3 h To this solution recooled to. 0 C 15 56 g of 1 2 amino 5 chlorophenyl 2 2 2 trifluoromethylethanone. 0 0696 mol was added as a solid portionwise over 5 min The reaction. mixture was allowed to stir at 0 C for 1 5 hours The reaction was quenched. at 0 C by dropwise addition of 700 mL of saturated aqueous ammonium. chloride solution The mixture was extracted with 2 times 400 mL portions of. ethyl acetate the combined organic phases were washed with brine and dried. over MgSO4 Removal of the drying agent and solvents left a yellow solid This. material was recrystallized from boiling hexanes 100 mL final volume to. afford 14 67 g of 2 2 amino 5 chlorophenyl 4 cyclopropyl 1 1 1 trifluoro 3. butyn 2 ol A second crop 2 1 g was obtained from concentrating the. mother liquors M p 153 154 C, Step B 6 Chloro 4 cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H. 3 1 benzoxazin 2 one, A solution of 2 2 amino 5 chlorophenyl 4 cyclopropyl 1 1 1 trifluoro 3. butyn 2 ol 15 00 g 0 0518 mol and 41 98 g 0 259 mol of 1 1. carbonyldiimidazole in 250 mL of dry THF was stirred under argon at 55 C for. 24 hours The solvent was removed on a rotary evaporator and the residue. was partitioned between 500 mL of ethyl acetate and 400 mL of water The. layers were separated and the aqueous phase was extracted once more with. ethyl acetate The combined ethyl acetate extracts were washed with 2 times. 200 mL of 2 aqueous HCl saturated aqueous NaHCO3 and brine Drying. over MgSO4 filtration and removal of the solvent in vacuo provided 16 42 g. of the title compound as a solid Recrystallization from ethyl acetate hexane. afforded 12 97 g of analytically pure 6 chloro 4 cyclopropylethynyl 4. trifluoromethyl 1 4 dihydro 2H 3 1 benzoxazin 2 one as a white crystals. Melting point 178 180 C, Step C 6 Chloro 1 1S camphanoyl 4 cyclopropylethynyl 4 trifluoromethyl. 1 4 dihydro 2H 3 1 benzoxazin 2 one,1424 Efavirenz. To a solution containing 6 chloro 4 cyclopropylethynyl 4 trifluoromethyl. 1 4 dihydro 2H 3 1 benzoxazin 2 one 12 97 g 0 041 mol 4. dimethylaminopyridine 1 02 g 0 0083 mol and camphanic acid chloride. 14 22 g 0 06556 mol in 350 mL of dry dichloromethane stirred under. argon in an ice bath was added triethylamine 22 84 mL 0 164 mol The. cooling bath was removed and the reaction was allowed to proceed at room. temperature After 75 min the reaction was judged complete by thin layer. chromatography SiO2 4 EtOAc in CHCl3 and the solution was diluted with. 500 mL of CHCl3 then washed with 10 citric acid 2X water 1X and brine. 1X Drying MgSO4 filtration and removal of the solvent in vacuo left a. colorless foam This material was triturated with 200 mL of boiling hexane On. cooling to room temperature the desired diastereomeric camphanate imide. precipitated The solid was collected on a frit washed with a little cold. hexanes and dried in vacuo to give 7 79 g of 6 chloro 1 1S camphanoyl 4. cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H 3 1 benzoxazin 2 one as. white crystals Melting point 164 165 C HPLC purity 99 2 254 nm. Step D 6 Chloro 4 cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H. 3 1 benzoxazin 2 one, 6 Chloro 1 1S camphanoyl 4 cyclopropylethynyl 4 trifluoromethyl 1 2.
dihydro 4 H 3 1 benzoxazin 2 one 7 50 g 0 01512 mol was dissolved in. 150 mL of n butanol at 60 C under an atmosphere of argon To this solution. was added 10 mL of 1 N HCl This solution was maintained at 60 C for 72 h. The mixture was neutralized with aqueous NaHCO3 and the n butanol was. removed in vacuo The residue was dissolved in 150 mL of THF and treated. with 50 mL of 2 N LiOH for 3 h at room temperature This mixture was diluted. with ethyl acetate and washed with two portions of water and one of brine. Drying MgSO4 filtration and removal of the solvent in vacuo gave a white. solid This material was recrystallized from hot hexane to give 3 43 g of 6. chloro 4 cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H 3 1 benzoxazin. 2 one as white crystals melting point 131 132 C D20 84 7 CHCl3. c 0 005 g mL, Step E 6 Chloro 4 cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H. 3 1 benzoxazin 2 one, The mother liquors from Step C above were purified by column. chromatography on silica gel using 10 ethyl acetate in hexanes as eluant. The pure undesired diastereomer a colorless foam was hydroylzed according. to Step D The enantiomeric benzoxazinone 6 chloro 4. cyclopropylethynyl 4 trifluoromethyl 1 4 dihydro 2H 3 1 benzoxazin 2 one. was obtained as white crystals Melting point 131 132 C D20 84 4. CHCl3 c 0 005 g mL,References, Young S D et al US Patent No 5 519 021 May 21 1996 Assignee Merck. and Co Inc Rahway NJ,Eletriptan hydrobromide 1425,ELETRIPTAN HYDROBROMIDE. Therapeutic Function Serotonin agonist, Chemical Name 1H Indole 3 2R 1 methyl 2 pyrrolidinyl methyl 5 2.
phenylsulfonyl ethyl ethyl monohydrobromide,Common Name Eletriptan hydrocbromide Relpax. Structural Formula, Chemical Abstracts Registry No 143322 58 1 Base 177834 92 3. Trade Name Manufacturer Country Year Introduced,Relpax Pfizer. Raw Materials,Phenyl vinyl sulfone Phosphine tri o tolyl. Palladium II acetate Triethylamine, Palladium on carbon R 5 Bromo 3 N methylpyrrolidinyl.
Hydrobromic acid methyl 1H indole,Hydrogen chloride. Manufacturing Process, A mixture of the appropriate phenyl vinyl sulfone tri o tolylphosphine. palladium II acetate triethlamine and R 5 bromo 3 N. methylpyrrolidinylmethyl 1H indole in anhydrous acetonitrle was heated at. reflux under nitrogen The resultant reaction mixture was evaporated under. reduced pressure and the residue was column chromatographed using silica. gel and elution with methylene chloride absolute ethanol ammonia to afford. the R 5 trans 2 phenylsulfonylethenyl 3 N methylpyrrolidin 2 ylmethyl. A solution of R 5 trans 2 phenylsulfonylethenyl 3 N methylpyrrolidin 2. ylmethyl 1H indole and 10 Pd C in ethanolic hydrogen chloride prepared. from absolute ethanol and acetyl chloride and N N dimethylformamide was. shaken under a hydrogen atmosphere at room temperature The resultant. reaction mixture was filtered through diatomaceous earth Celite trademark. washed with absolute ethanol and the combined filtrates were evaporated. under reduced pressure The residue was partitioned between ethyl acetate. and water The organic phase was separated washed with water brine dried. 1426 Emedastine fumarate, Na2SO4 and evaporated under reduced pressure to afford a oil product. Column chromatography of this product using silica gel and elution with. methylene chloride absolute ethanol ammonia afforded the appropriate R 5. 2 phenylsulfonylethyl 3 N methylpyrrolidin 2 ylmethyl 1H indole. The salt eletriptan hydrobromide may be produced by reaction of the R 5. 2 phenylsulfonylethyl 3 N methylpyrrolidin 2 ylmethyl 1H indole with. hydrobromic acid,References, Macor J E Wythes M J Patent cooperation treaty PCT WO 92 06973 April. EMEDASTINE FUMARATE,Therapeutic Function Antiallergic Antihistaminic.
Chemical Name 1H Benzimidazole 1 2 ethoxyethyl 2 hexahydro 4. methyl 1H 1 4 diazepin 1 yl E 2 butenedioate 1 2,Common Name Emedastine fumarate. Structural Formula,Chemical Abstracts Registry No 87233 62 3. Trade Name Manufacturer Country Year Introduced,Daren Kanebo Ltd Japan. Emedastine Alcon,Emadine Alcon UK,Raw Materials,2 Chlorobenzimidazole. N Methylpiperazine,2 Bromoethyl ethyl ether,Emylcamate 1427.
2 Chlorobenzimidazole,Fumaric acid,Manufacturing Process. Preparation of 2 4 methyl 1 piperazinyl benzimidazole A mixture of 2. chlorobenzimidazole 10 00 g and N mehylpiperazine 20 00 g is stirred at. 125 C for 5 hours A 10 aqueous sodium hydroxide 100 ml is added to the. reaction mixture and the precipitated crystals are separated by filtration The. filtrate is extracted with chloroform and the chloroform extract is evaporated. to dryness to give the same crystals The crystals are combined and. recrystallized from water methanol to give 2 4 methyl 1. piperazinyl benzimidazole 7 02 g as colorless needles m p 225 226 C. 2 4 Methyl 1 piperazinyl benzimididazole 5 00 g prepared as above is. dissolved in N N dimethylformamide 50 ml and thereto is added sodium. hydride concentration 50 1 50 g at room temperature and the mixture. is stirred for 30 minutes To the mixture is added 2 bromoethyl ethyl ether. 4 00 g and the mixture is stirred at 70 C for 10 hours To the reaction. mixture is added water 150 ml and the mixture is extracted with ethyl. acetate The extract is washed with water dried over anhydrous magnesium. sulfate and then concentrated to give a brown oily substance 5 40 g The. brown oily substance is treated with fumaric acid 3 26 g in hot ethanol The. crude crystals thus obtained are recrystallized from ethyl acetate ethanol to. give 1 2 ethoxy ethyl 2 4 methyl 1 piperazinyl benzimidazole 3 2. fumarate 6 31 g as colorless plates melting point 167 5 168 5 C. Elementary analysis for C22H30N4O7 Calcd C 57 13 H 6 54 N 12 11. Found C 57 04 H 6 44 N 12 02, 1 2 Ethoxy ethyl 2 4 methyl 1 piperazinyl benzimidazole can be prepared. using 2 chloro 1 2 ethoxy ethyl benzimidazole last one can be produced. from 2 bromoethyl ethyl ether 2 chlorobenzimidazole and N methylpiperazine. and fumaric acid there are obtained crude crystals which are recrystallized. from ethanol to give 1 2 ethoxy ethyl 2 4 methyl 1. piperazinyl benzimidazole 3 2 fumarate This product has the same physical. properties as those of the product above described. References, Iemura R et al US Patent No 4 430 343 Feb 7 1984 Assigned Kanebo. Ltd Tokyo JP,EMYLCAMATE,Therapeutic Function Tranquilizer. Chemical Name 3 Methyl 3 pentanol carbamate,Common Name.
1428 Enalapril maleate,Structural Formula,Chemical Abstracts Registry No 78 28 4. Trade Name Manufacturer Country Year Introduced,Striatin MSD US 1960. Raw Materials,3 Methyl 3 pentanol,Potassium cyanate. Trichloroacetic acid,Sodium carbonate,Manufacturing Process. 30 5 g of 3 methyl 3 pentanol 8 1 g of potassium cyanate and 16 3 g of. trichloroacetic acid are heated while stirring at 45 C to 50 C for 24 hours. neutralized by successive addition of anhydrous sodium carbonate The. precipitate is removed from the reaction mixture Unreacted 3 methyl 3. pentanol is distilled off and the residue is added to a small volume of distilled. water After precipitation and filtration the resulting 3 methyl 3 pentanol. carbamate is dried and recrystallized from petroleum ether MP 54 C to 55 C. References,Merck Index 3528, Melander B O and Hanshoff G US Patent 2 972 564 February 21 1961.
assigned to A B Kabi Sweden,ENALAPRIL MALEATE,Therapeutic Function Antihypertensive. Chemical Name L Proline 1 N 1 ethoxycarbonyl 3 phenylpropyl L. alanyl 1S 2Z 2 butenedioate 1 1,Common Name Enalapril maleate. Chemical Abstracts Registry No 76095 16 4 77549 59 8.

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