US2538795A - Alkamine esters of delta-cyclopentenyl-delta 2-cyclohexenylacetic acid - Google Patents

Alkamine esters of delta-cyclopentenyl-delta 2-cyclohexenylacetic acid Download PDF

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US2538795A
US2538795A US43544A US4354448A US2538795A US 2538795 A US2538795 A US 2538795A US 43544 A US43544 A US 43544A US 4354448 A US4354448 A US 4354448A US 2538795 A US2538795 A US 2538795A
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acid
cyclopentenyl
delta
cyclohexenylacetic
hydrochloride
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Moffett Robert Bruce
Hart Charlotte Anne
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GEORGE A BREON AND Co
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    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Definitions

  • esters have-the formula diethyl'amino, dipropylamino, d'i-butylamino, but'yl'propylamino, piperidyl, Z methyIpipEridyI, morpholinyl, thiomorph-olinyl, beta-hydroxyethylethylamino, etc. These maybe classed together. as. aliphatic tertiary-amino groups, the
  • heterocyclic' rings are distinctly non-aromatic in character and can be thought of as two alkyl groups joined together by a divalent bridge such as -Cl-I2-, -O- or --S.
  • Synthetic antispasmodics usuallyhave both amusculotropic (papaverine-like) neurotropic (athropine-like) action. It' is desirable that new compounds be introduced which have high neurotropic activitybut which lack the characteristic undesirable physiological sideeffects of atropine.
  • quaternaryammonium derivatives are obtained by the addition of alkyl or aralkyl esters of' inorganic acids or organic .sulfonic. acids, such. as .methyl' chloride,
  • the acid itself may be prepared by successive alkylationsof diethyl malonate or ethyl cyanoacetate with a A -cyclopentenyl halide and a, A -cyc1ohexeny1 halide, followed by hydrolysis and decarboxyla- ,tion of the disubstituted malonic or cyanoacetic esters to A -cyclopentenyl-A -cyclohexenylacetic acid.
  • the preferred method involves alkylation of diethyl A cyclopentenylma'lonate with 1,2-dibromocyclohexane to give directly diethyl A -cyclopenteny1-A -cyclohexenylmalonate.
  • the expected simple alkylation product of this reaction diethyl A -cyclopentenyl-2-zbromocyclohexylmalonate, is not isolated, hydrogen bromide being split out under the reaction conditions used to give the desired 2-3' double bond in the cyclon'exane ring.
  • the substituted malonio ester is hydrolyzed to the manolic acid by heating under pressure with a potassium hydroxide solution. Further heating under normal pressure causes elimination of one carboxyl group from the 'malonic' acid to give A -cyclopentenyleA -cyclohexenylacetic acid.
  • the reaction is effected bysimple admixture; :of the" two components" although heating isgenerally used to accelerate" the reaction.
  • Thef'ree basic ester is' obtained by addition of alkali totwort'zaction mixture.
  • the basic ester may be convertedto an acid addition .salt bysthez. addition,
  • the A -cyclopenteny1-A -cyclohexenylacetic acid is reacted with a tertiary-aminoalkanol using a mineral acid, such as sulfuric acid, as a catalyst, present in an amount greater than that necessary to neutralize the amino alcohol.
  • the free basic ester and its acid addition salts are obtained as in method (1)
  • the free basic ester and its acid addition salts are obtained as in method 1).
  • a metallic salt of A -cyclopentenyl-A -cyclohexenylacetic acid is heated or simply mixed with a tertiary-aminoalkyl halide. In this case the free basic ester is formed directly.
  • Quaternary ammonium salts are prepared by mixing the free basic ester with a lower alkyl or aralykyl ester of a strong inorganic acid or organic sulfonic acid, preferably in an inert organic solvent such as benzene or ether, with or without gentle heating.
  • the salt either crystallizes immediately or can be obtained by concentration of the solvent. 7
  • Example 1 Diethyl A -cyclopentenyl-M-cyCloheazenylmalonate.To a solution of '74 g. of sodium in 1.2 liters in absolute ethanol is added 271.2 g. of diethyl A -cyclopentenylmalonate. Most of the alcohol is distilled OE and toluene is added and distilled ofi until the boiling point reached is about 110 C. Enough more dry toluene is added to bring the volume to about 800 cc. and then 387.2 g. of 1,2-dibromocyclohexane is added slowly. After refluxing for two hours the mixture is cooled, 600 cc. of water is added and the layers are separated. The solvent is removed and the product is distilled through an efficient column giving about 202 g. (53.2%) of diethyl M-cyclopentenyl-A cyclohexenylmalonate, B. P. 124 C.
  • a -cycIopentenyl-A -cyclohexenylacetic acid (22 g.) is neutralized with an alcoholic solution of sodium methoxide and 14.5 g. of beta-diethylaminoethyl chloride in isopropyl alcohol is added.
  • the mixture is refluxed from three to four hours
  • Beta- (N -pz'peridyl) -ethyl n -cyclopentenyZ-A -cyclohexenylacetate and its hydrochloride A solution of 30 g. (0.134 m.) of A -cyclopentenyl-A -cyclohexenylacetyl chloride and 17.3 g. (0.134 m.) of beta-N-piperidylethanol in cc. of dry benzene is refluxed for four hours. Some of the product crystallizes at this point as the hydrochloride and is filtered off after cooling. This hydrochloride is neutralized with sodium carbonate solution.
  • the benzene filtrate is diluted with ether and extracted with water and dilute hydrochloric acid; the aqueous extracts are neutralized with sodium carbonate and combined with the other sodium carbonate solution obtained above.
  • the free basic ester is extracted with ether which is then dried over anhydrous sodium sulfate and concentrated.
  • the hydrochloride is made in the usual manner. It precipitates from ether as fine crystals in about 94% yield, M. P. 133-142" C.
  • Beta-dimethylamznoethyl M-cyclopentenyl-A2- cycloherenylacetate and its hydrochloride are prepared by methods previously described start,- ing with A -cyclopentenyl-A -cyclohexenylacetic acid and beta-dimethylaminoethanol.
  • Example 4 Z-dz'ethylamino-Z-propyl
  • a -cyclopentenyl-A cycloheacenylacetate and its hydrochloride are prepared by methods previously described startingwith A -cyclopentenyl-A -cyc1ohexenylacetic acid and 1-diethylamino-Z-propanol.
  • a substance of the group consisting of basic esters of the formula wherein Y is an alkylene bridge of 2-5 carbon atoms and N B is a tertiary-amino group of the class consisting of di-lower-alkyIamino, piperidyl and morpholinyl radicals; and acid ad.- dition and quaternary ammonium salts thereof.
  • a substance of the group consisting of betadimethylaminoalkyl A cyclopentenyl-M-cyclohexenylacetate having the formula and acid addition and quaternary ammonium salts thereof.

Description

Patented Jan. 23, 1951 .ALKAMINEE STERS OF A?.- GCLORENTENYL- A CYCIIOHEXENYLAGETIC 1 ACID Robert Bruce Mofliett, Kalamazoo, Mich, and
Charlotte Anne Hart, Kansas' City, Mo., assignors to; George A..Breon and Company, Kansas City, Mo.,. a. corporation ofyMissouri:
No-Drawing; Application .A-ngustlO, 194.8, Serial No. 4354i.
: 8, Claims. (01. zoo -2943') This. invention relatesto aminoalkyl. esters of -A cyclopentenylM-cyclohexenylaceticacids and to therapeutically acceptable salts thereof which are useful as antispasmodic agents. This. is a oontinuation in-partofour co-pending applica- 7 .tion,, S; N-. 639,405,. filed January 5,. 1946, now abandoned. These estershave-the formula diethyl'amino, dipropylamino, d'i-butylamino, but'yl'propylamino, piperidyl, Z methyIpipEridyI, morpholinyl, thiomorph-olinyl, beta-hydroxyethylethylamino, etc. These maybe classed together. as. aliphatic tertiary-amino groups, the
heterocyclic' rings are distinctly non-aromatic in character and can be thought of as two alkyl groups joined together by a divalent bridge such as -Cl-I2-, -O- or --S.
2' methyl sulfate; methylbenzenesulfonate, methyl p-toluenesulfonate, etc.
"Synthetic antispasmodics usuallyhave both amusculotropic (papaverine-like) neurotropic (athropine-like) action. It' is desirable that new compounds be introduced which have high neurotropic activitybut which lack the characteristic undesirable physiological sideeffects of atropine.
Our compounds are distinguished by high neurotropic activity, and,. in additiomseveral members of'the seriesshow antihistaminic. action.
. ,These compounds 'are generally used in the .form. of. water-soluble acid-addition salts or quaternary ammonium derivatives. The acids which .may be used to prepare the salts are those .hich produce, when combinedwith the basic esters, salts whose anions are relatively innocuous to the animal organism. in therapeutic doses of the salts, so that the beneficial physiological properties inherent in the basic esters are not vitiated by side-effects ascribable to theanions. Appropriate acid addition salts are those derived from; mineral acids. such: as hydrochloric. acid,
,hydrobromic acid, hydriodi'c, acid, and? sulfuric acidiandorganic acids such as acetic acid; citric acidandtartaric. acid. The quaternaryammonium derivatives are obtained by the addition of alkyl or aralkyl esters of' inorganic acids or organic .sulfonic. acids, such. as .methyl' chloride,
methyl bromide, methyl iodide, ethyl" bromide, propyl chloride, benzyl chloride," benzyl bromide,
Our compounds areconveniently prepared .by-
esterification of M-cyclopentenyl-A -cyclohexa nyl aceticacid with an amino alcohol. The acid itself may be prepared by successive alkylationsof diethyl malonate or ethyl cyanoacetate with a A -cyclopentenyl halide and a, A -cyc1ohexeny1 halide, followed by hydrolysis and decarboxyla- ,tion of the disubstituted malonic or cyanoacetic esters to A -cyclopentenyl-A -cyclohexenylacetic acid. The preferred method involves alkylation of diethyl A cyclopentenylma'lonate with 1,2-dibromocyclohexane to give directly diethyl A -cyclopenteny1-A -cyclohexenylmalonate. The expected simple alkylation product of this reaction, diethyl A -cyclopentenyl-2-zbromocyclohexylmalonate, is not isolated, hydrogen bromide being split out under the reaction conditions used to give the desired 2-3' double bond in the cyclon'exane ring. The substituted malonio ester is hydrolyzed to the manolic acid by heating under pressure with a potassium hydroxide solution. Further heating under normal pressure causes elimination of one carboxyl group from the 'malonic' acid to give A -cyclopentenyleA -cyclohexenylacetic acid.
The compounds of our invention, basic esters of A -cyclopentenylM-cyclohexenylacetic acid, and their acid addition salts are prepared by one of the-following methods; v
(1) An acid halide or anhydride of A -cycloc- :pentenyl-A cyclohexenylacetic acid is. reacted with a tertiary-aminoalkanol' ofthe formula.
atoms" and 'N= B 'isa tertiary amino: group. The reaction is effected bysimple admixture; :of the" two components" although heating isgenerally used to accelerate" the reaction. Thef'ree basic ester is' obtained by addition of alkali totheure'zaction mixture. The basic ester may be convertedto an acid addition .salt bysthez. addition,
prefer-abli -in non-aqueouszmedium;.zofia there:-
action and 3 peutically acceptable acid, such as hydrogen chloride in alcoholic solution.
(2) The A -cyclopenteny1-A -cyclohexenylacetic acid is reacted with a tertiary-aminoalkanol using a mineral acid, such as sulfuric acid, as a catalyst, present in an amount greater than that necessary to neutralize the amino alcohol. The free basic ester and its acid addition salts are obtained as in method (1) (3) The A -cyclopentenyl-A -cyclohexenylacetic acid is heated with a tertiary-aminoalkyl halide of the formula Z-YN=B, where Z is halogen (preferably chlorine or bromine) and Y and B have the same meaning as before. The free basic ester and its acid addition salts are obtained as in method 1).
(4) A metallic salt of A -cyclopentenyl-A -cyclohexenylacetic acid is heated or simply mixed with a tertiary-aminoalkyl halide. In this case the free basic ester is formed directly.
Quaternary ammonium salts are prepared by mixing the free basic ester with a lower alkyl or aralykyl ester of a strong inorganic acid or organic sulfonic acid, preferably in an inert organic solvent such as benzene or ether, with or without gentle heating. The salt either crystallizes immediately or can be obtained by concentration of the solvent. 7
Example 1 (a) Diethyl A -cyclopentenyl-M-cyCloheazenylmalonate.To a solution of '74 g. of sodium in 1.2 liters in absolute ethanol is added 271.2 g. of diethyl A -cyclopentenylmalonate. Most of the alcohol is distilled OE and toluene is added and distilled ofi until the boiling point reached is about 110 C. Enough more dry toluene is added to bring the volume to about 800 cc. and then 387.2 g. of 1,2-dibromocyclohexane is added slowly. After refluxing for two hours the mixture is cooled, 600 cc. of water is added and the layers are separated. The solvent is removed and the product is distilled through an efficient column giving about 202 g. (53.2%) of diethyl M-cyclopentenyl-A cyclohexenylmalonate, B. P. 124 C.
(b) A cyclopentenyl A cycloheccenylacetic acid.To a solution of 40 g. of potassium hydroxide in a 100 cc. of ethanol is added 40 g. of diethyl A cyclopentenyl-M- cyclohexenylmalonate. The mixture is placed in a bomb and heated to a 140-160" C. for 3 hours. After cooling, the product is dissolved in one liter in water and extracted with ether. Acidification of the aqueous layer gives an oil which is taken up in ether, washed with Water and dried over anhydrous sodium sulfate. The ether is removed and the residue is heated to 180 C. until no more car- .bon dioxide is evolved. The residue is distilled in vacuo and the fraction that distills at 101 C. under 0.01 mm. pressure is collected, giving A cyclopentenyl A cyclohexenylacetic acid, n =l.5120; d4 =l.0600.
(c) Beta-die'thylaminoethyl M-cyclopentenyln -cycloherenylacetate and its hydrochloride.- A -cycIopentenyl-A -cyclohexenylacetic acid (22 g.) is neutralized with an alcoholic solution of sodium methoxide and 14.5 g. of beta-diethylaminoethyl chloride in isopropyl alcohol is added. p The mixture is refluxed from three to four hours,
the solution is cooled and ether added to precipitate the salts. After filtration, the solvent is removed by vacuum disillation, and the residue is distilled at 116 C. under 0.02 mm. pressure. Thedistillate is taken up in dry etherand the ester hydrochloride is precipitated by the addition of anhydrous hydrogen chloride gas. The precipitated hydrochloride of beta-diethylaminoethyl A -cyclopentenyl-A -cyclohexenylacetate is filtered and dried; M. P. 108ll0.5 C.
Example 2 (a) A cyclopentenyl A cyclohexenylacetyl chZoride.- A solution of 41.2 g. (0.2 m.) of A -cyclopentenyl-A -cyclohexenylacetic acid and 35.7 g. (0.3 m.) of thionyl chloride in 100 cc. of dry benzene is refluxed for two and one-half hours. The solvent is removed by distillation, more benzene added and again concentrated to insure complete removal of excess thionyl chloride. The residue is distilled at reduced pressure giving about 41 g. of A -cyclopentenyl-n -cyclohexenylacetyl chloride, B. P. 110 C. (0.3 mm.); n =1.5180; d4 =l.0974.
(b) Beta- (N -pz'peridyl) -ethyl n -cyclopentenyZ-A -cyclohexenylacetate and its hydrochloride.A solution of 30 g. (0.134 m.) of A -cyclopentenyl-A -cyclohexenylacetyl chloride and 17.3 g. (0.134 m.) of beta-N-piperidylethanol in cc. of dry benzene is refluxed for four hours. Some of the product crystallizes at this point as the hydrochloride and is filtered off after cooling. This hydrochloride is neutralized with sodium carbonate solution. The benzene filtrate is diluted with ether and extracted with water and dilute hydrochloric acid; the aqueous extracts are neutralized with sodium carbonate and combined with the other sodium carbonate solution obtained above. The free basic ester is extracted with ether which is then dried over anhydrous sodium sulfate and concentrated. The product distills at 139 C. g. (59%) of beta-(N-piperidyD-ethyl A -cyclopentenyl-A -cyclohexenylacetate; m 1 .5070; dl =l.0222.
The hydrochloride is made in the usual manner. It precipitates from ether as fine crystals in about 94% yield, M. P. 133-142" C.
Example 3 Beta-dimethylamznoethyl M-cyclopentenyl-A2- cycloherenylacetate and its hydrochloride are prepared by methods previously described start,- ing with A -cyclopentenyl-A -cyclohexenylacetic acid and beta-dimethylaminoethanol. The free basic ester boils at C. (0.05 mm.), n =l.4948,' d4 =1.00l2, and its hydrochloride has the M. P. 129-133.5 C.
Example 4 Z-dz'ethylamino-Z-propyl A -cyclopentenyl-A cycloheacenylacetate and its hydrochloride are prepared by methods previously described startingwith A -cyclopentenyl-A -cyc1ohexenylacetic acid and 1-diethylamino-Z-propanol. The free basic ester boils at 116 C. (0.03 mm.), n =1.l882; d4 =0.9786, and its hydrochloride has the M. P. 1l8l20 C.
Example 5 I Beta- (N -morpholinyl) -et hyl A -cyclopentenyl- M-cyclohe11:ehylacetafe and its hydrochloride are prepared by methods previously described starting With A -cyclopentenyl-zl -cyclohexenylacetic acid and beta-(N-morpholinyl)-ethanol. free basic ester boils at 130 C. (0.02 mm.), n .5083; d4 =1.0655, and its hydrochloride (0.07 mm.), giving about 25.1
The
Example 6 Gamma-diethylaminopropyl A cycZopantenyL n -cyclohexclnylaceiate and its hydrochloride are prepared by methods previously described starting with A -cyciopentenyl-A -cyc1ohexenylacetic acid and gamma-diethylaminopropanoi. The free basic ester boils at 131 C. (0.07 mm.), n =1.4900; d4 =0.976'1, and its hydrochloride has the M. P. l15118 C.
We claim:
1. A substance of the group consisting of basic esters of the formula wherein Y is an alkylene bridge of 2-5 carbon atoms and N=B is a tertiary-amino group of the class consisting of di-lower-alkyIamino, piperidyl and morpholinyl radicals; and acid ad.- dition and quaternary ammonium salts thereof.
2. A substance of the group consisting of basic esters of the formula wherein Y is an alkylene bridge of 2-5 carbon atoms and R and R are lower alkyl groups; and acid addition and quaternary ammonium salts thereof.
3. A substance of the group consisting of basic esters of the formula CH2CH2 CH2 CHrCz where Y is an alkylene bridge of 2-5 carbon atoms; and acid addition and quaternary ammonium salts thereof.
4. A substance of the group consisting of betadiethylaminoethyl A -cycl0penteny1-A -cyc1ohexenylacetate having the formula CH2CH3 and acid addition and quaternary ammonium salts thereof.
5. A substance of the group consisting of beta- 6 (N piperidyl) ethyl M-cyclopentenyl-A -cyclo hexenylacetate havingthe formula CHzCHz and acid addition and quaternary ammonium salts thereof.
6. A substance of the group consisting of betadimethylaminoalkyl A cyclopentenyl-M-cyclohexenylacetate having the formula and acid addition and quaternary ammonium salts thereof.
7. A substance of the group consisting of l-diethylamino 2 propyl A cyclopentenyl A cyclohexenylacetate having the formula and acid addition and quaternary ammonium salts thereof.
8. A substance of the group consisting of gamma-diethylaminopropyl A -cyclopentenyl-A cyclohexenylacetate having the formula CHzCHz and acid addition and quaternary ammonium salts thereof.
ROBERT BRUCE MOFFETT. CHARLOTTE ANNE HART.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,677,123 Adams July 17, 1928 2,265,184 Miescher et a1. Dec. 19, 1941 2,351,833 Northey et al June 20, 1944 2,417,208 Martin et al. Nov. 11, 1947 FOREIGN PATENTS Number Country Date 93,341 Sweden Nov. 19, 1938 532,943 Great Britain Feb. 4, 1941 220,975 Switzerland Aug. 1, 1942 221,219 Switzerland Aug. 17, 1942 221,519 Switzerland Sept. 1, 1942 Certificate of Correction Pateut N o. 2,538,795
ROBERT BRUCE MOFFETT ET AL.
It ishereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows:
Column 2, line 32, for manolio read malom'c; column 6, line 27, for -2 propyl read -2-p7-0;03 Z; and that the said Letters Patent should be read as corrected above, so that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 3rd day of April, A. D. 1951.
THOMAS F. MURPHY,
Assistant Commissioner of Patents.
January 23, 1951 i

Claims (1)

1. A SUBSTANCE OF THE GROUP CONSISTING OF BASIC ESTERS OF THE FORMULA
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2662887A (en) * 1951-07-21 1953-12-15 Warner Hudnut Inc Substituted esters of cyclic alcohols
US2684370A (en) * 1951-07-21 1954-07-20 Warner Hudnut Inc Certain aminoalkyl-2-thienyl-cycloalkenyl thiolacetates
US2684369A (en) * 1951-07-21 1954-07-20 Warner Hudnut Inc Certain thienyl, cycloalkenyl acetamides
DE961349C (en) * 1951-07-20 1957-04-04 Sterling Drug Inc Process for the production of highly effective anticholinergic compounds
US2889353A (en) * 1955-12-14 1959-06-02 Univ Michigan Alkamine esters of alpha-(delta1-cycloalkenyl)-beta-hydroxy-aliphatic acids and preparation thereof
US3018222A (en) * 1956-08-28 1962-01-23 Ravensberg G M B H Central stimulant and appetite depressant composition

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1677123A (en) * 1927-08-25 1928-07-17 Abbott Lab Cyclopentenyl alkyl acetic acid
GB532943A (en) * 1938-08-05 1941-02-04 Chem Ind Basel Manufacture of alkamine esters and quaternary salts thereof
CH220975A (en) * 1938-08-05 1942-04-30 Chem Ind Basel Process for the preparation of a basic ester.
CH221219A (en) * 1938-08-05 1942-05-15 Chem Ind Basel Process for the preparation of a basic ester.
US2351833A (en) * 1942-04-08 1944-06-20 American Cyanamid Co N(alkyl,beta-4-morpholylalkyl) aminoalkanol esters
US2417208A (en) * 1943-08-04 1947-03-11 Geigy Ag J R Basic esters of monoalkyl isobutyl acetic acids

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1677123A (en) * 1927-08-25 1928-07-17 Abbott Lab Cyclopentenyl alkyl acetic acid
GB532943A (en) * 1938-08-05 1941-02-04 Chem Ind Basel Manufacture of alkamine esters and quaternary salts thereof
US2265184A (en) * 1938-08-05 1941-12-09 Ciba Pharm Prod Inc Basic esters and process of preparing same
CH220975A (en) * 1938-08-05 1942-04-30 Chem Ind Basel Process for the preparation of a basic ester.
CH221219A (en) * 1938-08-05 1942-05-15 Chem Ind Basel Process for the preparation of a basic ester.
CH221519A (en) * 1938-08-05 1942-05-31 Chem Ind Basel Process for the preparation of a basic ester.
US2351833A (en) * 1942-04-08 1944-06-20 American Cyanamid Co N(alkyl,beta-4-morpholylalkyl) aminoalkanol esters
US2417208A (en) * 1943-08-04 1947-03-11 Geigy Ag J R Basic esters of monoalkyl isobutyl acetic acids

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE961349C (en) * 1951-07-20 1957-04-04 Sterling Drug Inc Process for the production of highly effective anticholinergic compounds
US2662887A (en) * 1951-07-21 1953-12-15 Warner Hudnut Inc Substituted esters of cyclic alcohols
US2684370A (en) * 1951-07-21 1954-07-20 Warner Hudnut Inc Certain aminoalkyl-2-thienyl-cycloalkenyl thiolacetates
US2684369A (en) * 1951-07-21 1954-07-20 Warner Hudnut Inc Certain thienyl, cycloalkenyl acetamides
US2889353A (en) * 1955-12-14 1959-06-02 Univ Michigan Alkamine esters of alpha-(delta1-cycloalkenyl)-beta-hydroxy-aliphatic acids and preparation thereof
US3018222A (en) * 1956-08-28 1962-01-23 Ravensberg G M B H Central stimulant and appetite depressant composition

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