US3489760A - N,n - methyl cyclohexyl - 2 - ethyl - 3,3 - diphenyl - propene - (2) - yl-amine and the salts thereof - Google Patents
N,n - methyl cyclohexyl - 2 - ethyl - 3,3 - diphenyl - propene - (2) - yl-amine and the salts thereof Download PDFInfo
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- US3489760A US3489760A US634430A US3489760DA US3489760A US 3489760 A US3489760 A US 3489760A US 634430 A US634430 A US 634430A US 3489760D A US3489760D A US 3489760DA US 3489760 A US3489760 A US 3489760A
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- ethyl
- propene
- diphenyl
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
- C07C215/32—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton containing hydroxy groups and carbon atoms of two six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Definitions
- This invention relates to the tertiary amines of 3,3-diphenyl propyl amine compounds of the formula Wherein R is alkyl, for example alkyl having up to 8 carbon atoms, preferably having 28 carbon atoms, for example ethyl, propyl, butyl;
- R and R is each selected from the group consisting of alkyl and cycloalkyl, and preferably each is a lower alkyl or lower cycloalkyl and is a group as is conventionally present in organic amino compounds for therapeutic use and preferably containing up to about 6 carbon atoms, and each of the groups can be, for example, methyl, butyl, ethyl, propyl, isopropyl, isobutyl, secondary butyl, isoamyl, hexyl, isohexyl, and cyclohexyl.
- Preferred products of formula (I) are those wherein R is ethyl, propyl or butyl, especially ethyl.
- Particular compounds found to be well suited for the purposes of the invention are: N,N-dimethyl-2-ethyl-3,3- diphenyl-propene-(Z)-yl-arnine, N,N-dipropyl-2-ethyl-3,3- diphenyl-propene- (2 -yl-amine, N,N-methyl cyclohexyl-2- ethyl-3,3-diphenyl-propene-(2)-yl-amine, and medicinally acceptable acid addition salts of these compounds or other medicinally acceptable salts.
- the compounds of the above formula valuable therapeutic properties which render them useful as vasopressors and in particular for increasing blood pressure, stimulating the heart muscle, accelerating the heart rate and 3,489,760 Patented Jan. 13, 1970 increasing cardiac output. Of outstanding importance is that they diminish or eliminate the undesirable depressive side effects of morphine or respiration.
- the compounds can be used in the form of medically acceptable acid addition salts.
- the vasopressor effect is accomplished by administration of a therapeutic amount of the compound used.
- ethyl-3,3-diphenyl-propene-(2)-yl-amine and medicinally acceptable acid addition salts with hydrochloric, hydrobromic, or hydroiodic acid. Acid addition salts are preferred.
- the salts are crystalline solids which are soluble in water and therefore constitute an advantageous embodiment of this invention.
- the disclosed organic bases form salts with a variety of inorganic and organic acids conventionally used for therapeutic application or organic amino or imino bases and including hydrochloric, hydrobromic, hydroiodic, sulfuric, phosphoric, citric, lactic, maleic, acetic, benzoic, oxalic and related or similar acids.
- the resulting salt crystallizes out of suitably concentrated solution on chilling or standing or may be precipitated by addition of a solvent, such as ether or benzene in which the salt is insoluble.
- the invention is characterized in that the Leuckart reaction is used for preparation of the compounds.
- the corresponding primary or secondary amine that is, a compound as in Formula I above, except that R and/or R is hydrogen
- the organic acid is formic acid.
- the starting primary or secondary amines can be produced by the methods disclosed in application Ser. No. 231,018, filed Oct. 16, 1962, and now abandoned and assigned to the assignee hereof.
- the residue is made alkaline, extracted with ether, and the separated ether part, dried with sodium sulfate, and distilled.
- the residue is dissolved in methanolic hydrochloric acid and through addition of ether is obtained the N,N-dipropyl-Z-ethyl-3,3- diphenyl-propene- (2 -ylamine hydrochloride.
- EXAMPLE 3 14.1 g. of 2-ethyl-3,3-diphenyl-propene-(2)-yl-amine are added under cooling to a mixture of 13.8 g. formic acid and 1.5 ml. water. To the reaction mixture are added 11.4 ml. of 35% aqueous formaldehyde solution, and the whole subsequently heated for 15 hours to 110 C. After the cooling one acidifies with 54 ml. concentrated hydrochloric acid, and the excess formic acid/formaline solution is distilled-01f in vacuum on the Water bath. The residue is made alkaline with soda lye, extracted with ether, the separated ether part dried with sodium sulfate and distilled.
- 2-alkyl such as 2-propyl derivatives can be made by the procedure of the examples by corresponding change in the starting material.
- I.V. Blood pressure increase of 20-30 mm.
- I.V. Blood pressure increase of 30-60 mm.
- the 1-(3- hydroxyphenyl)-1-hydroxy-2-N-ethyl-amino ethane hydrochloride in a dosage of 1-4 mg./kg., a blood pressure increase of 20-60 mm. Hg, lasting 4 to 8 minutes, is found.
- the compounds may be given in dosage form hypo dermically or intramuscularly in the form of HCl salt, or in the form of their salts in isotonic physiologically acceptable solutions, as for example water saline or peanut oil. Locally, they may be used in solution as a spray and in ointment.
- the compounds of the invention also constitute valuable tools for use in medical research, as for instance in connection with animal experiments and in particular in the study of their effect on the blood pressure by stimulating the contraction of the muscular tissue of the capillaries and arterioles.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,489,760 N,N METHYL CYCLOHEXYL 2 ETHYL 3,3 DI- PHENYL PROPENE (2) YL-AMINE AND THE SALTS THEREOF Horst Eissler, Ludwigshafen, Mundenheim, Germany, as-
signor to Gebruder Giuliui G.m.b.H., Ludwigshafen (Rhine), Germany, a corporation of Germany No Drawing. Continuation of application Ser. No.
313,425, Oct. 3, 1963, which is a division of application Ser. No. 231,018, Oct. 16, 1962. This application Apr. 24, 1967, Ser. No. 634,430 Claims priority, application (zrmany, Oct. 19, 1961, 33 3 G Int. Cl. C07c 87/40; A61k 27/00 US. Cl. 260-2955 1 Claim ABSTRACT OF THE DISCLOSURE Compounds of the formula:
This invention relates to the tertiary amines of 3,3-diphenyl propyl amine compounds of the formula Wherein R is alkyl, for example alkyl having up to 8 carbon atoms, preferably having 28 carbon atoms, for example ethyl, propyl, butyl;
R and R is each selected from the group consisting of alkyl and cycloalkyl, and preferably each is a lower alkyl or lower cycloalkyl and is a group as is conventionally present in organic amino compounds for therapeutic use and preferably containing up to about 6 carbon atoms, and each of the groups can be, for example, methyl, butyl, ethyl, propyl, isopropyl, isobutyl, secondary butyl, isoamyl, hexyl, isohexyl, and cyclohexyl.
Preferred products of formula (I) are those wherein R is ethyl, propyl or butyl, especially ethyl.
Particular compounds found to be well suited for the purposes of the invention are: N,N-dimethyl-2-ethyl-3,3- diphenyl-propene-(Z)-yl-arnine, N,N-dipropyl-2-ethyl-3,3- diphenyl-propene- (2 -yl-amine, N,N-methyl cyclohexyl-2- ethyl-3,3-diphenyl-propene-(2)-yl-amine, and medicinally acceptable acid addition salts of these compounds or other medicinally acceptable salts.
The compounds of the above formula valuable therapeutic properties which render them useful as vasopressors and in particular for increasing blood pressure, stimulating the heart muscle, accelerating the heart rate and 3,489,760 Patented Jan. 13, 1970 increasing cardiac output. Of outstanding importance is that they diminish or eliminate the undesirable depressive side effects of morphine or respiration. The compounds can be used in the form of medically acceptable acid addition salts. The vasopressor effect is accomplished by administration of a therapeutic amount of the compound used.
ethyl-3,3-diphenyl-propene-(2)-yl-amine, and medicinally acceptable acid addition salts with hydrochloric, hydrobromic, or hydroiodic acid. Acid addition salts are preferred. The salts are crystalline solids which are soluble in water and therefore constitute an advantageous embodiment of this invention. The disclosed organic bases form salts with a variety of inorganic and organic acids conventionally used for therapeutic application or organic amino or imino bases and including hydrochloric, hydrobromic, hydroiodic, sulfuric, phosphoric, citric, lactic, maleic, acetic, benzoic, oxalic and related or similar acids. In many instances, the resulting salt crystallizes out of suitably concentrated solution on chilling or standing or may be precipitated by addition of a solvent, such as ether or benzene in which the salt is insoluble.
The invention is characterized in that the Leuckart reaction is used for preparation of the compounds. In this process, the corresponding primary or secondary amine (that is, a compound as in Formula I above, except that R and/or R is hydrogen) is contacted with an organic acid and an aldehyde of the group R or R for reductive alkylation to form a compound according to Formula I. Preferably, the organic acid is formic acid.
The starting primary or secondary amines can be produced by the methods disclosed in application Ser. No. 231,018, filed Oct. 16, 1962, and now abandoned and assigned to the assignee hereof.
EXAMPLE I N,N-methyl cyclohexyl-2-ethyl-3,3-diphenyl-propene- (2 -yl-amine-hydrochloride.
6.4 g. of N-cyclohexyl-2-ethyl-3,3-diphenyl-propene- (2)-yl-amine are treated under cooling with 2.3 g. formic acid and 0.25 ml. water. Further, 1.9 ml. aqueous formaldehyde solution are added (35%), and the mixture heated for 15 hours to 110 C. After the cooling, the material is acidified with 9 m1. concentrated hydrochloric acid and distilled in vacuum until dry. The residue is treated with diluted soda lye, extracted with ether, and the ether part dried with sodium sulfate and distilled. The residue is dissolved in methanolic hydrochloric acid, and through addition of ether is obtained the N,N-methylcyclohexyl 2-ethyl-3,3-diphenyl-propene-(2)-yl-amine hydrochloride crystalline.
Melting point: 170173 C. Yield: of the theory.
EXAMPLE 2 N,N-dipropyl-2-ethyl-3,3-diphenyl-propene-( 2)- yl-amine-hydrochloride 4.7 g. of Z-ethyl-3,3-diphenyl-propene-(2)-yl-amine are added under cooling to a mixture of 4.6 g. of formic acid and 0.5 ml. water. One adds 3.2 ml. propionic aldehyde and heats the mixture for 15 hours to C. After the cooling 18 ml. concentrated hydrochloric acid are added and the excess formic acid and the excess propionic aldehyde is distilled off in vacuum. The residue is made alkaline, extracted with ether, and the separated ether part, dried with sodium sulfate, and distilled. The residue is dissolved in methanolic hydrochloric acid and through addition of ether is obtained the N,N-dipropyl-Z-ethyl-3,3- diphenyl-propene- (2 -ylamine hydrochloride.
Melting point: 221-222 C.
EXAMPLE 3 14.1 g. of 2-ethyl-3,3-diphenyl-propene-(2)-yl-amine are added under cooling to a mixture of 13.8 g. formic acid and 1.5 ml. water. To the reaction mixture are added 11.4 ml. of 35% aqueous formaldehyde solution, and the whole subsequently heated for 15 hours to 110 C. After the cooling one acidifies with 54 ml. concentrated hydrochloric acid, and the excess formic acid/formaline solution is distilled-01f in vacuum on the Water bath. The residue is made alkaline with soda lye, extracted with ether, the separated ether part dried with sodium sulfate and distilled. There remains only an oil, which is dissolved in methanolic hydrochloric acid. Through addition of ether to the solution, the hydrochloride of the N,N-dimethyl-2-ethyl-3,3-diphenyl-propene-(2)-yl-arnine crystallizes out.
Melting point: l98200 C. Yield: 84% of the theory.
Other 2-alkyl, such as 2-propyl derivatives can be made by the procedure of the examples by corresponding change in the starting material.
UTILITY DATA Compounds of Formula I The effect on blood pressure in cats under urethane chloralose narcosis was noted.
N,N-dimethyl-2-ethyl-3,3-diphenyl propene (2) ylamine as hydrochloride, gluconate, nicotinate or methane sulfonate:
l rug/kg. I.V.: Blood pressure increase of 15-20 mm.
Hg, lasting about 30 minutes;
2 rug/kg. I.V.: Blood pressure increase of 25-40 mm.
Hg, lasting about 1 to 2 hours.
N,N-dipropyl-2-ethyl-3,3-diphenyl propene (2) ylamine as hydrochloride, gluconate, nicotinate or methane sulfonate:
1 mgJkg. I.V.: Blood pressure increase of 20-30 mm.
Hg, lasting about 1 hour.
2 mg./kg. I.V.: Blood pressure increase of 30-60 mm.
Hg, lasting about 1 /2 to 4 hours.
For lower starting blood pressure the blood pressure increase effect is stronger and lasts longer than for normal or high starting blood pressure.
Under equal test conditions, for example, the 1-(3- hydroxyphenyl)-1-hydroxy-2-N-ethyl-amino ethane hydrochloride, in a dosage of 1-4 mg./kg., a blood pressure increase of 20-60 mm. Hg, lasting 4 to 8 minutes, is found.
correspondingly, ephedrine elfects in a dosage of 1-3 mg./kg., a blood pressure increase of 20-5" mm. Hg, which lasts up to about 40 minutes maximum.
COMPOSITIONS The compounds may be given in dosage form hypo dermically or intramuscularly in the form of HCl salt, or in the form of their salts in isotonic physiologically acceptable solutions, as for example water saline or peanut oil. Locally, they may be used in solution as a spray and in ointment.
The exact dosage in each instance is entirely dependent on the effect sought to be achieved, the mode of administration employed and the degree of caution which must be observed. In any instance, there is employed at least that amount of the compounds, i.e., active agent, necessary to produce the desired physiological effect, but less than that amount producing an undesired toxic effect.
The compounds of the invention, as can be readily appreciated, also constitute valuable tools for use in medical research, as for instance in connection with animal experiments and in particular in the study of their effect on the blood pressure by stimulating the contraction of the muscular tissue of the capillaries and arterioles.
What is claimed is:
1. N,N-methylcyclohexyl-2-ethyl-3,3-diphenyl-propene- (2)-yl-amine and medicinally acceptable salts thereof.
References Cited UNITED STATES PATENTS 3,190,920 6/1965 Spickett 260-570 FOREIGN PATENTS 525,752 6/ 1956 Canada. 624,117 5/ 1949 Great Britain. 627,139 7/1949 Great Britain.
OTHER REFERENCES Adams et al., Organic Reactions, vol. 5, pp. 307-8 1949 Kjaer et al., Acta Chemica Scand., vol. 5, pp. 1146-48 1) ROBERT V. I-IINES, Primary Examiner US. Cl. X.R.
2226153? l UNITED STATES PATENT OFFICE wig 55 CERTIFICATE OF CORRECTION 6, Patent Ne. 3 ,489 760 T I D t January 134 1970 U Invent fl Horst Eissler It is certified that error appears in the above-identified patent and that said Letters Patent arehereby corrected as shown below:
l 1. C01. 2, line S cancel "ethyl-3,3.. .medicinally" and insert therefore --The salts are desirably I hydrochlorides or medicinally-.
2. Col. 4, line 5, change 20-5" to --20-50--.
j SIGNED AND SEALED .f JUN 2 3 1970 f G i- Attest:
Emma u Fletcher. 3:. mm: E. comm. .m. i 8 Officer Oomissioner of Patents
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG33376A DE1149002B (en) | 1961-10-19 | 1961-10-19 | Process for the preparation of hypertensive salts of N, N-dialkyl-2-ethyl-3, 3-diphenyl-propen- (2) -yl-amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3489760A true US3489760A (en) | 1970-01-13 |
Family
ID=7124680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US634430A Expired - Lifetime US3489760A (en) | 1961-10-19 | 1967-04-24 | N,n - methyl cyclohexyl - 2 - ethyl - 3,3 - diphenyl - propene - (2) - yl-amine and the salts thereof |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3489760A (en) |
| DE (1) | DE1149002B (en) |
| FR (1) | FR1395525A (en) |
| GB (1) | GB960302A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6022895A (en) * | 1997-03-14 | 2000-02-08 | Gruenenthal Gmbh | Substituted amino compounds and their use as substances having an analgesic effect |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1135926A (en) * | 1966-02-24 | 1968-12-11 | Geistlich Soehne Ag | Pharmaceutical compositions containing bisphenyl-alkenylamine derivatives |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB624117A (en) * | 1946-12-07 | 1949-05-27 | Wellcome Found | Improvements in and relating to the preparation of substituted allylamines and propylamines |
| GB627139A (en) * | 1947-05-28 | 1949-07-29 | Wellcome Found | Improvements in and relating to the preparation of quaternary ammonium salts of substituted propanolamines, allylamines and propylamines |
| CA525752A (en) * | 1956-06-05 | V. Petersen Poul | Antispasmodic unsaturated tertiary amines | |
| US3190920A (en) * | 1961-05-19 | 1965-06-22 | Smith Kline French Lab | 1-ortho-lower alkyl-phenyl-1-phenyl-2 lower alkyl-3-diloweralkylamino-1-propanols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH294173A (en) * | 1950-10-09 | 1953-10-31 | Sharp & Dohme Inc | Process for the preparation of a quaternary ammonium compound. |
| DE1051281B (en) * | 1955-07-05 | 1959-02-26 | Bayer Ag | Process for the preparation of derivatives of 1-aryl-3-aminopropan-1-ols |
| NL110122C (en) * | 1957-02-05 |
-
1961
- 1961-10-19 DE DEG33376A patent/DE1149002B/en active Pending
-
1962
- 1962-10-04 FR FR19889A patent/FR1395525A/en not_active Expired
- 1962-10-18 GB GB39471/62A patent/GB960302A/en not_active Expired
-
1967
- 1967-04-24 US US634430A patent/US3489760A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA525752A (en) * | 1956-06-05 | V. Petersen Poul | Antispasmodic unsaturated tertiary amines | |
| GB624117A (en) * | 1946-12-07 | 1949-05-27 | Wellcome Found | Improvements in and relating to the preparation of substituted allylamines and propylamines |
| GB627139A (en) * | 1947-05-28 | 1949-07-29 | Wellcome Found | Improvements in and relating to the preparation of quaternary ammonium salts of substituted propanolamines, allylamines and propylamines |
| US3190920A (en) * | 1961-05-19 | 1965-06-22 | Smith Kline French Lab | 1-ortho-lower alkyl-phenyl-1-phenyl-2 lower alkyl-3-diloweralkylamino-1-propanols |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6022895A (en) * | 1997-03-14 | 2000-02-08 | Gruenenthal Gmbh | Substituted amino compounds and their use as substances having an analgesic effect |
Also Published As
| Publication number | Publication date |
|---|---|
| GB960302A (en) | 1964-06-10 |
| DE1149002B (en) | 1963-05-22 |
| FR1395525A (en) | 1965-04-16 |
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