US2186976A - Tkialkylacetamides having satu - Google Patents
Tkialkylacetamides having satu Download PDFInfo
- Publication number
- US2186976A US2186976A US2186976DA US2186976A US 2186976 A US2186976 A US 2186976A US 2186976D A US2186976D A US 2186976DA US 2186976 A US2186976 A US 2186976A
- Authority
- US
- United States
- Prior art keywords
- acetamide
- carbon atoms
- butyl
- general formula
- alkyl groups
- 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 - Lifetime
Links
- 125000004432 carbon atoms Chemical group C* 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 230000002048 spasmolytic Effects 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- 239000000812 cholinergic antagonist Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N Papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
- 150000003869 acetamides Chemical class 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQLFIBRQIBBUHS-UHFFFAOYSA-N 2,2-dibutylhexanenitrile Chemical compound CCCCC(CCCC)(CCCC)C#N WQLFIBRQIBBUHS-UHFFFAOYSA-N 0.000 description 4
- ZJLWAVUWLDHAKS-UHFFFAOYSA-N 2-butyl-2-propylhexanamide Chemical compound CCCCC(CCC)(C(N)=O)CCCC ZJLWAVUWLDHAKS-UHFFFAOYSA-N 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- -1 for example Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002825 nitriles Chemical group 0.000 description 4
- 229960001789 papaverine Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 2
- UHMNFOXASJKWDP-UHFFFAOYSA-N 2,2-dibutylhexanamide Chemical compound CCCCC(CCCC)(CCCC)C(N)=O UHMNFOXASJKWDP-UHFFFAOYSA-N 0.000 description 2
- PSKBXMRNHIJYCD-UHFFFAOYSA-N 2,2-diethylhexanamide Chemical compound CCCCC(CC)(CC)C(N)=O PSKBXMRNHIJYCD-UHFFFAOYSA-N 0.000 description 2
- ACBLZFZDCOGNHD-UHFFFAOYSA-N 2,2-dipropylpentanamide Chemical compound CCCC(CCC)(CCC)C(N)=O ACBLZFZDCOGNHD-UHFFFAOYSA-N 0.000 description 2
- YPBCGKKPKIAIGT-UHFFFAOYSA-N 2-butyl-2-ethylhexanamide Chemical class CCCCC(CC)(C(N)=O)CCCC YPBCGKKPKIAIGT-UHFFFAOYSA-N 0.000 description 2
- 210000001772 Blood Platelets Anatomy 0.000 description 2
- VUXGIXOLNRYMFY-UHFFFAOYSA-N C(C)C(C(=O)N)(CCC(C)C)CCC(C)C Chemical compound C(C)C(C(=O)N)(CCC(C)C)CCC(C)C VUXGIXOLNRYMFY-UHFFFAOYSA-N 0.000 description 2
- WASORPCLBXVOJZ-UHFFFAOYSA-N C(C)C(C(=O)N)(CCC)CC.C(C)C(C(=O)N)(CC)CC Chemical compound C(C)C(C(=O)N)(CCC)CC.C(C)C(C(=O)N)(CC)CC WASORPCLBXVOJZ-UHFFFAOYSA-N 0.000 description 2
- UECDIRIGLYFKSD-UHFFFAOYSA-N C(C)C(C(=O)N)(CCCCCC)CCCCCC Chemical compound C(C)C(C(=O)N)(CCCCCC)CCCCCC UECDIRIGLYFKSD-UHFFFAOYSA-N 0.000 description 2
- VDJDRKHGSLPEJB-UHFFFAOYSA-N C(CC(C)C)C(C(=O)N)(CCC(C)C)CCC(C)C Chemical compound C(CC(C)C)C(C(=O)N)(CCC(C)C)CCC(C)C VDJDRKHGSLPEJB-UHFFFAOYSA-N 0.000 description 2
- FZKLIKUSSBVPTH-UHFFFAOYSA-N C(CC)C(C(=O)N)(CCCC)CCC Chemical compound C(CC)C(C(=O)N)(CCCC)CCC FZKLIKUSSBVPTH-UHFFFAOYSA-N 0.000 description 2
- UTIAUJMGDKPXOJ-UHFFFAOYSA-N C(CC)C(C(=O)N)(CCCCC)CCCCC Chemical compound C(CC)C(C(=O)N)(CCCCC)CCCCC UTIAUJMGDKPXOJ-UHFFFAOYSA-N 0.000 description 2
- JRLDISHCINEWOA-UHFFFAOYSA-N C(CCC)C(C(=O)N)(CCCCC)CCCC Chemical compound C(CCC)C(C(=O)N)(CCCCC)CCCC JRLDISHCINEWOA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 210000000936 Intestines Anatomy 0.000 description 2
- 229940053973 Novocaine Drugs 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229960003207 Papaverine Hydrochloride Drugs 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N Procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003301 hydrolyzing Effects 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002557 soporific Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C07C231/065—By hydration using metals or metallic ions as catalyst
Definitions
- This invention relates to trialkylacetamides having saturated alkyl groups and a method of making the same.
- the present invention is based on the discovery that the tertiary saturated alkyl substitutedacetic acid amides with from 12 to 17 C-atoms,
- R g in which R, R and R" indicate the same or different saturated alkyl groups such that in the case of the saturated trialkylaceta'mides with 12 carbon atoms R, R and R" constitute alkyls with at least 3 carbon atoms, compared with those described by Fromherz exhibit an unexpectedly good spasmolytic action.
- the hydrolysis can be carried out instead of with sulphuric acid by heating with water to 180 to 200 C., if desired with the addition of an emulsifying agent such as the sodium salt of di-isopropylnaphthalene-B-su1phonic acid.
- an emulsifying agent such as the sodium salt of di-isopropylnaphthalene-B-su1phonic acid.
- Example 2 50 parts of tri-n-butyl-acetonitrile B. P. 142 to 146 C. under 17 mm. pressure, 300 parts of butyl or amyl alcohol and 60 parts of potassium hydroxide in 10 parts of water are boiled with stirring under a reflux condenser for hours, the alcohol is thereupon removed by steam distillation and the residue extracted with benzene. From the benzene solution is obtained in the customary manner the amide, which passes over in a vacuum of 12 mm. at 183 C. It solidifies to white needles which have the M. P. 60 to 61 C. It is easily soluble in ether, petrol-ether benzene, alcohol, and chloroform, insoluble in water.
- Example 3 Triisoamyl acetonitrile, obtained according to U. S. Patent 1,958,653 from acetonitrile, sodium amide and isoamyl bromide, yields on saponification triisoamyl acetamide of the boiling point 198 C. at a vacuum of 14 mm. and the melting point 67 to 685 C. It crystallizes from petrol ether in White platelets.
- a process for the manufacture of a trialkylacetamide with saturated alkyl groups and of strong spasmolytic action comprising saponifying tri-n-butyl acetonitrile to the corresponding acetamide.
- a process for the manufacture of substances having a high spasmolytic action comprising hydrolyzing tertiary nitriles with at least 12 and at most 17 carbon atoms in the molecule, of the general formula:
- R, R and R" indicate saturated alkyl groups all higher than methyl, at least two of such groups having at least four carbon atoms.
- a trialkylacetamide of strong spasmolytic action having at least 12 and at most 1'7 carbon atoms in the molecule, and of the general formula:
- R, R and R" indicate saturated alkyl groups, at least two of such groups having at least four carbon atoms.
- R, R and R indicate saturated alkyl groups, at least two of such groups having each at least 4 carbon atoms and the third at least 3 carbon atoms, the total number of carbon atoms in the compound not exceeding 1'7.
- R, R and R" indicate saturated alkyl groups of 3 to 5 carbon atoms, at least two of such groups having more than 3 but no more than 5 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 16, 1940 UNITEDSTATES PATENT OFFlCE TRIALKYLACE TAIHIDES HAVING SATU- RATED ALKYL GROUPS AND A METHOD OF MAKING THE SAME Karl Junkmanm Berlin, and Hans-Georg Allardt, Philippsthal, Kreis Teltow, Germany, assignors to Schering Aktiengesellschaft, a corporation of Germany No Drawing. Application January 8,
Serial No. 119,658. In Germany August 16,
10Claims. (01.260 66!) This invention relates to trialkylacetamides having saturated alkyl groups and a method of making the same.
By the researches of Fromherz, Arch. -f. exp. Pathologie und Pharmakologie, vol. 1'73, page 78, it has become known that the substituted acetamides possess peripheral paralysing (spasmolytic) properties. This assertion is accompanied on page 83 by three examples, which are, however, only very weakly active acetamides.
The present invention is based on the discovery that the tertiary saturated alkyl substitutedacetic acid amides with from 12 to 17 C-atoms,
' manufactured according to known processes from tertiary nitriles of the general formula:
R" g in which R, R and R" indicate the same or different saturated alkyl groups such that in the case of the saturated trialkylaceta'mides with 12 carbon atoms R, R and R" constitute alkyls with at least 3 carbon atoms, compared with those described by Fromherz exhibit an unexpectedly good spasmolytic action. I
By comparing the different trialkylacetamides on a superior rabbit intestine maintained permanently in Tyrode solution containing barium, the individual preparations being standardised against novocaine hydrochloride as comparative preparation, the following results are obtained:
Activity number papaverino HO]- solution=l00 Acetamide examined C-number I. Saturated triallcylacetamides containing up to ZZJ-C-atams M ethyl-diethyl-ace tamide iiiiiiiii Triethyl-acetamide Diethyl-n-propyl-acetamide i Methyl-dipropyl-acotamide Ethyl-clipropyl-acetamide Diethyl-butyl-acetamide. Tripropyl-acetamide. i Ethyl-dibutylacetamides i H; Unsaturated trialkylacetamidas containing up to IZ-C-utoms Diethyl-allyl-acetamidc M othyl-diallyl-acetamide i. Ethyl-diallyl-acetamide. i n-Propyl-diallyl'acetainide i Isopropyl-diallyl-acetamide i n-Butyl-dia]lyl-aoetamide 'Iriallyl-acetamide Activitynumber papaverine H01- solution=l00 Acetamide examined O-number III. Saturated trialkylacetamides contaming 12-17- C-atoms (according to the invention) Dipropyl-butyl-acetamide -l2 100. Propyl-dibutyl-acetamide 13 110 Tributyl-acetamide i. 14 130 Ethyl-di-isoamyl-acetamide. 14 187. 5 Ethyl-dihexyl-acetamide 16 125. O Tri-isoamyl-acetamide 17 125. 0 Propyl-diamyl-acetamide. 15 125. 0 Butyl-diainyl-acetamide 8 Dibutyl-amyl-acetamide In these experiments novocaine' hydrochloride was equal to 1/75 papaverine hydrochloride. It
- was thereforepossible by a simple calculation to bring the numbers'obtained into relation with those given by Fromherz'; who uses papaverine as standard and makes this equal to 100.
From this table .it ,is clearly "seen that the strong effects obtained with the tertiary saturated amides of this invention were not to be foreseen. v
In addition it should be remarked that the hitherto known acetamides with small C-number examined by Fromherz are fairly strong scporifics, while the new substances according to the present invention even in large doses have practically 'no soporific effect which is extremely separating extracted with a solvent immiscible with water, for example, benzene, the extract washed with sodium carbonate solution and the amide produced therefrom in the customary manner. It is separated from small quantities of starting material by vacuum distillation. The amide has the B. P. 176 C. under 16 mm. pressure, the M. P. 69 to 70 C. and constitutes a white crystal powder which easily dissolves in ether, alcohol, petrol-ether and benzene.
o H N Found 73. 47 12.8 6.9 Calculated 13.2 12. 6. 5s
The hydrolysis can be carried out instead of with sulphuric acid by heating with water to 180 to 200 C., if desired with the addition of an emulsifying agent such as the sodium salt of di-isopropylnaphthalene-B-su1phonic acid.
(b) 19.5 parts of di-n-butyl-n-pr0pyl-acetonitrile are dissolved in 200 parts of alcohol and 48 parts of 10% hydrogen peroxide and 0.8 part of caustic soda in a little Water added. The whole is heated with stirring gradually to 40 to 60 C., neutralised after completion of the hydrolysis with acid and the alcohol evaporated. The residue recrystallised from dilute alcohol yields white needles of M. P. 69-'70 C., the pure dibutyl-propyl-acetamide.
Example 2 50 parts of tri-n-butyl-acetonitrile B. P. 142 to 146 C. under 17 mm. pressure, 300 parts of butyl or amyl alcohol and 60 parts of potassium hydroxide in 10 parts of water are boiled with stirring under a reflux condenser for hours, the alcohol is thereupon removed by steam distillation and the residue extracted with benzene. From the benzene solution is obtained in the customary manner the amide, which passes over in a vacuum of 12 mm. at 183 C. It solidifies to white needles which have the M. P. 60 to 61 C. It is easily soluble in ether, petrol-ether benzene, alcohol, and chloroform, insoluble in water.
For acceleration of the saponification it can be carried out suitably in autoclaves at a temperature of 150 to C. Otherwise the process is conducted as set forth above.
Example 3 Triisoamyl acetonitrile, obtained according to U. S. Patent 1,958,653 from acetonitrile, sodium amide and isoamyl bromide, yields on saponification triisoamyl acetamide of the boiling point 198 C. at a vacuum of 14 mm. and the melting point 67 to 685 C. It crystallizes from petrol ether in White platelets.
Of course, in a similar manner other saturated trialkylacetamides having at least 12 and at most 17 carbon atoms in the molecule may be obtained from the corresponding trialkylacetonitriles.
What we claim is:
1. A process for the manufacture of a trialkylacetamide with saturated alkyl groups and of strong spasmolytic action, comprising saponifying tri-n-butyl acetonitrile to the corresponding acetamide.
2. Tri-n-butyl acetamide of the general formula CmHzcON and the melting point 60-61 C.
3. A process for the manufacture of substances having a high spasmolytic action, comprising hydrolyzing tertiary nitriles with at least 12 and at most 17 carbon atoms in the molecule, of the general formula:
atoms in the molecule, of the general formula:
RI! in which R, R and R" indicate saturated alkyl groups all higher than methyl, at least two of such groups having at least four carbon atoms.
5. A trialkylacetamide of strong spasmolytic action having at least 12 and at most 1'7 carbon atoms in the molecule, and of the general formula:
a ccoum R in which R, R and R" indicate saturated alkyl groups, at least two of such groups having at least four carbon atoms.
6. As a spasmolytic agent, and trialkylacetamide of strong spasmolytic action having more than 12 but no more than 17 carbon atoms in the molecule, and of the general formula:
w-coozvm in which R, R and R" indicate saturated alkyl groups all higher than methyl.
'7. A trialkylacetamide of strong spasmolytic action of the general formula:
in which R, R and R indicate saturated alkyl groups, at least two of such groups having each at least 4 carbon atoms and the third at least 3 carbon atoms, the total number of carbon atoms in the compound not exceeding 1'7.
8. A trialkylacetamide of strong spasmolytic action of the general formula:
rv-ccoxm in which R, R and R" indicate saturated alkyl groups of 3 to 5 carbon atoms, at least two of such groups having more than 3 but no more than 5 carbon atoms.
9. As a spasmolytic agent, n-propyl-di-n-butyl acetamide of the general formula C13H2'1ON and the melting point 69-70 C. from dilute alcohol.
10. As a spasmolytic agent, tri-isoamyl acetamide of the general formula C1'1H35ON and the melting point 67-68.5 C.
KARL JUNKMANN. HANS-GEORG ALLARDT.
Publications (1)
Publication Number | Publication Date |
---|---|
US2186976A true US2186976A (en) | 1940-01-16 |
Family
ID=3431009
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US2186976D Expired - Lifetime US2186976A (en) | Tkialkylacetamides having satu |
Country Status (1)
Country | Link |
---|---|
US (1) | US2186976A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2529521A (en) * | 1946-07-01 | 1950-11-14 | Schering Corp | Trisubstituted acetic acids |
US2937117A (en) * | 1953-06-19 | 1960-05-17 | Chimie Atomistique | Process for lowering high blood cholesterol levels |
US3052703A (en) * | 1957-12-30 | 1962-09-04 | Shell Oil Co | N-acylated-amino derivatives of halogenated bicyclo (2, 2, 1) hept-5-en-2-yl compounds |
US3317603A (en) * | 1963-09-27 | 1967-05-02 | Monsanto Co | Improvement in the preparation of n-vinyl-n-methylacetamide |
US3666809A (en) * | 1969-10-08 | 1972-05-30 | Mitsubishi Chem Ind | Method for the production of acrylamide crystals |
FR2209555A1 (en) * | 1972-12-11 | 1974-07-05 | Labaz | |
US4296255A (en) * | 1972-04-18 | 1981-10-20 | Wilkinson Sword Limited | Acyclic carboxamides having a physiological cooling effect |
-
0
- US US2186976D patent/US2186976A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2529521A (en) * | 1946-07-01 | 1950-11-14 | Schering Corp | Trisubstituted acetic acids |
US2937117A (en) * | 1953-06-19 | 1960-05-17 | Chimie Atomistique | Process for lowering high blood cholesterol levels |
US3052703A (en) * | 1957-12-30 | 1962-09-04 | Shell Oil Co | N-acylated-amino derivatives of halogenated bicyclo (2, 2, 1) hept-5-en-2-yl compounds |
US3317603A (en) * | 1963-09-27 | 1967-05-02 | Monsanto Co | Improvement in the preparation of n-vinyl-n-methylacetamide |
US3666809A (en) * | 1969-10-08 | 1972-05-30 | Mitsubishi Chem Ind | Method for the production of acrylamide crystals |
US4296255A (en) * | 1972-04-18 | 1981-10-20 | Wilkinson Sword Limited | Acyclic carboxamides having a physiological cooling effect |
FR2209555A1 (en) * | 1972-12-11 | 1974-07-05 | Labaz |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2186976A (en) | Tkialkylacetamides having satu | |
US2208485A (en) | Process for the manufacture of disubstituted carbamic acid esters of phenols containing a basic substituent | |
CH622497A5 (en) | ||
US2460144A (en) | Hydroxyphenyl alkanolamines | |
US2816895A (en) | Basic benzilic esters and a process of preparing them | |
US2960507A (en) | Piperidine compounds | |
US2544076A (en) | Quaternary ammonium salts of di-and tri-(dialkylaminoalkoxy)-benzenes | |
US2941002A (en) | Beta-hydroxy carboxylic acid amides substituted at the nitrogen atom | |
US2864825A (en) | Pyrrolidines | |
US2881165A (en) | alpha-alpha-diphenyl-gamma-hexamethyleneiminobutyramide | |
US2832777A (en) | 2-aminophenyl-3-methylmorpholines | |
JUNKMANN et al. | Other Classes | |
US2315661A (en) | Manufacture of nitrile compounds | |
US2490834A (en) | Benzhydryl beta hydroxy alkyl amines | |
US2744931A (en) | Anhydrochlortetracycline | |
US3112311A (en) | 2-phenyl-5, 6-dimethyl-morpholines and 2-phenyl-5, 6-tetramethylene-morpholines | |
US2454949A (en) | 4-dialkylaminoalkylamino-6-methoxyquinoline | |
US1976923A (en) | Amino-alkyl-esters of the carboxy-alkoxy-amino-diphenyls | |
US2750390A (en) | Nicotinic acid ester | |
US2948722A (en) | 1-(1, 2, 3, 4-tetrahydroisoquinolino)-omega-amino-3-ethinyl-3-hydroxy alkanes | |
US2336093A (en) | 1-o-hydroxyphenoxy-3-alkoxy-2-propanols and/or-2-propanones and their manufacture | |
US2117207A (en) | Amino acids | |
US3096374A (en) | New carboxylic acid amides substituted at the nitrogen atom and beta-carbon atom and process for their manufacture | |
US2876261A (en) | Alpha-di-chloroacetamido-beta-chloro-p-nitropropiophenone and method of production | |
US2103272A (en) | Process for the production of beta-methylcholine ethers and salts thereof |