US3257420A - Carboxylic acids alpha-substituted by at least one cyclic radical - Google Patents

Carboxylic acids alpha-substituted by at least one cyclic radical Download PDF

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Publication number
US3257420A
US3257420A US174684A US17468462A US3257420A US 3257420 A US3257420 A US 3257420A US 174684 A US174684 A US 174684A US 17468462 A US17468462 A US 17468462A US 3257420 A US3257420 A US 3257420A
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alpha
naphthyl
acid
mol
product
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Expired - Lifetime
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US174684A
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Szarvasi Etienne
Neuvy Liliane
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Merck Sante SAS
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LIPHA SAS
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Priority claimed from FR853642A external-priority patent/FR1289597A/fr
Priority claimed from FR860401A external-priority patent/FR80103E/fr
Priority claimed from FR862174A external-priority patent/FR1318M/fr
Priority claimed from FR885619A external-priority patent/FR81162E/fr
Application filed by LIPHA SAS filed Critical LIPHA SAS
Priority to US485085A priority Critical patent/US3282964A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • n is an odd number at most equal to 3
  • R is a member of the group comprising the l-naphthyl and l-naphthylmethyl radicals
  • R is a member of the group comprising the furyl and tetrahydrofuryl radicals and-when n denotes the number l and R the naphthyl radicalthe vinyl and 1- propenyl radicals, as also their sodium salts, their alkyl and dialkylaminoethyl esters, their hydrazides and their 2-amidoethanol derivatives, and the corresponding ethyl malonates, nitriles and amides.
  • R and R have the same meanings as before and R is a lower alkyl radical, is saponified and decarboxylated by means of an alkali in the presence of an alcohol, preferably benzyl alcohol.
  • alkyl malonates are preferably obtained by reaction of a sodium alcoholate with an alkyl malonate mono-substituted by one of the radicals R and R (011 followed by condensation of the sodium derivative obtained with the halide of formula R (CH or R X, in which X denotes chlorine or bromine, depending upon whether the radical already attached to the. alkyl malonate is R or R (CH Disubstituted ethyl malonates of the formula in which 11, R and R have the same meanings as before, are new compounds.
  • nitriles are preferably obtained by treatment of nitrile of the general formula R CH CN or with sodamide, followed by condensation of the sodium derivative obtained with the halide of the general formula R (CH X or R X, depending upon whether the nitrile is of formula R CH CN or R,- ;(CH ),,CH CN.
  • Alpha-substituted nitriles of the formula OH-CN R2(CH2)11 in which n, R and R have the same meanings as before, are new compounds.
  • the sodium salts and the alkyl and dialkylaminoethyl esters of the preceding acids are obtained by neutralisa tion or esterification of the corresponding acids, which thus constitute intermediate products in the preparation of their derivatives.
  • the toxicities of the compounds of the invention expressed by the 50% lethal dose orally or intraperitoneally administered in the rat, are the following (in mg./kg.):
  • the above acids and sodium salts, mixed with or dissolved in appropriate excipients and adjuvants, may be administered for the treatment of atherosclerosis in dosages between 0.010 g. and 2 g. per day by the oral, rectal or parenteral route;
  • the dialkylaminoethyl esters possess a therapeutic antiinflammatory activity.
  • the diethylaminoethyl ester of alpha-l-naphthylhexen-delta-4-oic acid possesses psychoenergetic activity which is useful in the treatment of traumatic conditions, which is much greater than that of the dimethylaminoethyl ester of para-chlorophenoxyacetic acid, which is a known therapeutic compound.
  • the diethylaminoethyl ester of 1-naphthylpenten delta-4-oic acid exhibits in the Magnus test on the isolated intestine of the rabbit a spasmolytic activity which is ten times greater than that of papaverine.
  • hydrazides constitute intermediate products in the synthesis of the substituted hydr-azines described in the French patent application of December 11, 1961, in the name of the applicants, which constitute inhibitors of monoa'minooxydase and coronary vasodilators.
  • ethoxide is prepared by introducing 9 g. (0.4 atom) of sodium into 256 cc. of absolute ethanol. There are added thereto 96 g. (0.4 mol.) of ethyl furfurylmalonate, and the mixture is boiled for 5 minutes while being well stirred. After cooling, 70.4 g. (0.4 mol.) of 1-chloromethylnaphthalene are added drop by drop through a dropping funnel, whereafter the mixture is heated under reflux for 24 hours and extracted with 25 benzene.
  • Example 5 Alpha- (1-naphthyl) tctrahydrofurylvaleronitrile
  • Example 6.-Alpha+(1-naphthyl)hexen-delta-4-0ic nitrile C H N. -(M 22-1.28.)
  • Sodium methylate may be employed as condensing agent instead of sodamide.
  • Example 7 Alpha (I-naphthyl)penten-delta- 4-0ic nitrile 11.1 g. of sodamide (0.238 mol. of NaNH in cc. of dry ether are reacted as in Example 3 with 37.5 g. (0.224 mol.) of l-naphthylacetonitrile and 28 g. (0.223 mol.) of allyl bromide.
  • Gravimetric aaalysis --.Calculated: C percent, 8694; H percent, 6.31; N percent, 6.76. Found: C percent, 86.94, 86.87; H percent, 6.29, 6.15; N percent, 7.1-1, 7.04.
  • Example 8 Beta-(1-naphthyl)beta'Jw-ylisobutyric acid The product, covered with a layer of hexane, crystallises rapidly, after scraping of the wall with a rod, into substantially white crystals.
  • the recrystallisation is effected as follows:
  • Its sodium salt has a melting point of 260-262 C.
  • W /OH-COOCH3 LO CHz 25 g. (0.089 mol.) of beta-(1-naphthyl)heta-furylisobutyric acid are esterified by heating under reflux with 150 cc. of absolute methanol in the presence of 0.5 cc.
  • the redistilled product has the following constants:
  • the sodium salt has a melting point of 261 C. with decomposition (on the capillary tube). It is a hygroscopic product.
  • Example 13 Methyl alpha- (1 Jmph thylm'ethyl deltatetrahydrofury lvalerate 26.5 g. (0.0845 mol.) of alpha-(1-naphthylmethyl)deltatetrahydrofuryl valeric acid are esterified by the procedure of Example 9.
  • the redistilled product has the following constants:
  • the sodium salt takes the form of white crystals which V are insoluble in cold water and soluble in boiling water,
  • the alpha-( l-naphthyl)furylpropionic amide is obtained alone by the procedure described in the following Example 15, which consists in hydrolysing nitrile in ethanol in the presence of the stoichiometric quantity of potassium hydroxide and limiting the duration of the reaction to half that necessary for producing the acid.
  • Example 16 Methyl alpha-(1-naphthyl)farylpr0pionate C ONHz 27 g. (0.101 mol.) of alpha-(l-naphthyDfurylpropionic acid, 150 cc. of absolute methanol and 0.5 cc. of concentrated sulphuric acid are heated under reflux for 6 hours. After the usual treatment, distillation gives 19 g. of pale yellow oil distilling at 172 172.5 C./1 mm. Hg.
  • the redistilled product has the following constants:
  • the preceding distillate is taken up in 25 cc. of ethyl acetate, and white crystals are formed on the addition of hexane. After three recrystallisations, the product takes the form of white crystals having a melting point of 135 C. (heating stage). 7
  • the sodium salt has a melting point of 250-25 1 C. (capillary tube).
  • Example 22 Methyl alpha-(l-naphthyl)tetrahydrofurylprapionate o 1.1- 00cm
  • U 22 g. (0.0812 mol.) of alpha-(1-naphthyl)tetrahydrofurylpropionic acid are esterified as in Example 9. There are obtained 17.5 g. of pale yellow viscous liquid (yield 75.5%).
  • the redistilled product has a boiling point of 157-158 C./0.36 mm. Hg.
  • Example 23 --Ne0pentyl alpha-(1 -naplzthyl)tetrahydrofurylpropionale 27 (0.1 mol.) of alpha-(l-naphthyl)tetrahydrofurylpropionic acid, prepared as described in Example 20, are esterified with neopentyl alcohol. Distillation gives 20 g. (yield about 59%) of viscous yellow liquid distilling at 182-185 C./1 mm. Hg.
  • the redistilled product has the following constants:
  • the redistilled product which has a honey-yellow color, has a melting point of 191 C./0.36 mm. Hg.
  • Example 25 --Alpha (1-naphthyl)delta tetrahydrofurylvaleric acid L /'0 11-0 0 OH h (01 2)::
  • Example 26 Diethylaminoethyl alpha-(1 -naphthyl)- delta-retrahydrofurylvalerate 29.8 g. (0.1 mol.) of alpha-(l-naphthyDtetrahydrofurylvaleric acid, prepared as described in Example 22, are esterified with diethylaminoethanol 'by the procedure described in Example 11.
  • the redistilled product has the following constants:
  • CH-OONH2 CH3CH CHCI I2 22 g. (0.1 mol.) of alpha-(l-naphthyl)hexen-delta-4- oic nitrile are hydrolysed by the procedure of Example 15. There are obtained 21 g. of yellow product (yield 87.7%). After four recrystallisations from ethyl acetate, the product has a melting point of 1121-122" C. It sublimates in the neighbourhood of this temperature.
  • Example 30 Methyl alpha-(I-naplztlzyl)hexen-delta- 24 g. (0.1 mol.) of alpha-(l-naphthyl)hexen-delta-4- oic acid, prepared as described in Example 28, are esterified with methyl alcohol by the procedure of Example 9.
  • the redistilled product has the following constants:
  • Example 31 --Dietl1ylamin0ethyl alpha-(1 -naphthyl) hexen-delta-4-0ate 24 g. (0.1 mol.) of alpha-(l-naphthyl)hexen delta-4-oic acid are e-sterified with d'iethylaminoethyl alcohol by the procedure described in Example 11.
  • This compound may be solubilised by salification with an acid, more especially hydrochloric acid. It can be directly obtained in the form of its chloride by heating the starting acid with beta-chloroethyl-N-diethylamine in isopropanol.
  • M.P. 125-127 C. (heating stage), with sublimation starting at 100 C.
  • Example 33 Alpha-(1-naphthyl)penten-delta-4-0ic acid
  • Example 34 Diethylaminoethyl ester of alpha-(1 -naphthyl)penten-delta-4-0ic acid
  • Empirical formula C21H27NO2. M 325.42.
  • the redistilled product has the following physical constants:
  • Y 1 A compound of the formula CH-C O OH R2( 2)n in which n, is an odd number at most equal to 3, R is a member of the group consisting of the l-naphthyl and l-naphthylmethyl radicals, and R is a member of the group consisting of the furyl and tetrahydrofuryl radicals andwhen n denotes the number 1 and R the naphthyl radical-the vinyl and l-propenyl radicals. 2.
  • R is a member of the group consisting of the l-naphthyl .and l-naphthylmethyl radicals, and R is a member of the group consisting of the furyl and tetrahydrofuryl radicals and-when n denotes the number 1 and R the naphthyl radical-the vinyl and l-propenyl radicals. 3. Beta-(l-naphthyl) beta'-furylisobutyric acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US174684A 1961-02-23 1962-02-21 Carboxylic acids alpha-substituted by at least one cyclic radical Expired - Lifetime US3257420A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US485085A US3282964A (en) 1962-02-21 1965-09-03 New alpha-substituted carboxylic acid derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR853642A FR1289597A (fr) 1961-02-23 1961-02-23 Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation
FR860401A FR80103E (fr) 1961-02-23 1961-04-28 Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation
FR862174A FR1318M (fr) 1961-05-16 1961-05-16 Nouveaux acides carboxyliques alpha-substitués a propriétés hypocholésterolémiantes.
FR885619A FR81162E (fr) 1962-01-23 1962-01-23 Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation

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US (1) US3257420A (enrdf_load_stackoverflow)
BE (1) BE613547A (enrdf_load_stackoverflow)
CH (2) CH464172A (enrdf_load_stackoverflow)
DE (3) DE1693019B2 (enrdf_load_stackoverflow)
GB (1) GB999589A (enrdf_load_stackoverflow)
NL (1) NL274986A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3334105A (en) * 1962-12-04 1967-08-01 Lipha Carboxylic acids substituted in the alpha-position by at least one aminoheterocyclic, and processes for the preparation thereof
US3445574A (en) * 1962-09-20 1969-05-20 Lipha Compositions and method for arresting spasms with the diethylaminoethyl ester of beta-(1-naphthyl)-beta'-tetrahydrofurylisobutyric acid
US3686307A (en) * 1969-02-07 1972-08-22 Standard Oil Co Conversion of nitriles to amides in the presence of alkaline catalysts
US3699151A (en) * 1967-08-14 1972-10-17 Bruno Cavalleri Pharmacologically active compounds
US3956323A (en) * 1972-01-03 1976-05-11 Hoffmann-La Roche Inc. Furan, benzofuran and tetrahydrofuran carboxylic acid esters
US4131615A (en) * 1976-08-06 1978-12-26 A. Wasserman S.P.A. Furan derivative for use as pharmaceutical product particularly for the treatment of rheumatic illnesses
US4224226A (en) * 1977-07-22 1980-09-23 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of N-substituted α-ketocarboxylic acid amides
US4652583A (en) * 1985-04-23 1987-03-24 Lipha, Lyonnaise Industrielle Pharmaceutique Use of naftidrofuryl to regenerate nerve fibers
US5329054A (en) * 1993-07-19 1994-07-12 Albemarle Corporation Decarboxylation process

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2003363A1 (de) 1969-01-30 1970-08-06 Ciba Geigy Verfahren zum Faerben und Bedrucken von Textilien mit Kuepen- und Reaktivfarbstoffen

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2834789A (en) * 1955-02-15 1958-05-13 Sadolin & Holmblad As Process of preparing lower lakyl 2, 3, 6-trihydroxybenzoate, and intermediates therefor
US2841594A (en) * 1958-07-01 Production of beta-furoic acids
US2843607A (en) * 1954-07-13 1958-07-15 Air Liquide Process of preparing esters
US2937117A (en) * 1953-06-19 1960-05-17 Chimie Atomistique Process for lowering high blood cholesterol levels
US3013023A (en) * 1959-02-27 1961-12-12 Ueno Ryuzo Process for the production of 5-nitrofuryl acrylic acid
US3057777A (en) * 1957-10-28 1962-10-09 Lilly Co Eli Method of reducing cholesterol level of the blood
US3060198A (en) * 1959-10-06 1962-10-23 Du Pont Tetracyanofuran

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2841594A (en) * 1958-07-01 Production of beta-furoic acids
US2937117A (en) * 1953-06-19 1960-05-17 Chimie Atomistique Process for lowering high blood cholesterol levels
US2843607A (en) * 1954-07-13 1958-07-15 Air Liquide Process of preparing esters
US2834789A (en) * 1955-02-15 1958-05-13 Sadolin & Holmblad As Process of preparing lower lakyl 2, 3, 6-trihydroxybenzoate, and intermediates therefor
US3057777A (en) * 1957-10-28 1962-10-09 Lilly Co Eli Method of reducing cholesterol level of the blood
US3013023A (en) * 1959-02-27 1961-12-12 Ueno Ryuzo Process for the production of 5-nitrofuryl acrylic acid
US3060198A (en) * 1959-10-06 1962-10-23 Du Pont Tetracyanofuran

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3445574A (en) * 1962-09-20 1969-05-20 Lipha Compositions and method for arresting spasms with the diethylaminoethyl ester of beta-(1-naphthyl)-beta'-tetrahydrofurylisobutyric acid
US3334105A (en) * 1962-12-04 1967-08-01 Lipha Carboxylic acids substituted in the alpha-position by at least one aminoheterocyclic, and processes for the preparation thereof
US3699151A (en) * 1967-08-14 1972-10-17 Bruno Cavalleri Pharmacologically active compounds
US3686307A (en) * 1969-02-07 1972-08-22 Standard Oil Co Conversion of nitriles to amides in the presence of alkaline catalysts
US3956323A (en) * 1972-01-03 1976-05-11 Hoffmann-La Roche Inc. Furan, benzofuran and tetrahydrofuran carboxylic acid esters
US4131615A (en) * 1976-08-06 1978-12-26 A. Wasserman S.P.A. Furan derivative for use as pharmaceutical product particularly for the treatment of rheumatic illnesses
US4224226A (en) * 1977-07-22 1980-09-23 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of N-substituted α-ketocarboxylic acid amides
US4652583A (en) * 1985-04-23 1987-03-24 Lipha, Lyonnaise Industrielle Pharmaceutique Use of naftidrofuryl to regenerate nerve fibers
US5329054A (en) * 1993-07-19 1994-07-12 Albemarle Corporation Decarboxylation process

Also Published As

Publication number Publication date
CH464172A (fr) 1968-10-31
NL274986A (enrdf_load_stackoverflow)
GB999589A (enrdf_load_stackoverflow) 1965-07-28
DE1493912A1 (de) 1969-07-10
DE1693019A1 (de) 1972-03-30
CH447200A (fr) 1967-11-30
BE613547A (fr) 1962-08-06
DE1493933A1 (de) 1969-06-04
DE1693019B2 (de) 1975-11-13

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