US2993831A - Polyalkylenebisaniline anesthetics - Google Patents
Polyalkylenebisaniline anesthetics Download PDFInfo
- Publication number
- US2993831A US2993831A US742752A US74275258A US2993831A US 2993831 A US2993831 A US 2993831A US 742752 A US742752 A US 742752A US 74275258 A US74275258 A US 74275258A US 2993831 A US2993831 A US 2993831A
- Authority
- US
- United States
- Prior art keywords
- ether
- compound
- anesthetic
- dimethylaniline
- polyalkylenebisaniline
- 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
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- 239000003193 general anesthetic agent Substances 0.000 title description 5
- 229940035674 anesthetics Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- 206010002091 Anaesthesia Diseases 0.000 claims description 6
- 230000037005 anaesthesia Effects 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical class CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003444 anaesthetic effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- -1 hydrochloric Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- QNWMFJDRMZWZNN-UHFFFAOYSA-N 2,6-dimethylaniline;hydron;chloride Chemical compound Cl.CC1=CC=CC(C)=C1N QNWMFJDRMZWZNN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NKPZCZPKVHUSBO-UHFFFAOYSA-N n,n'-bis(2,6-dimethylphenyl)butane-1,4-diamine Chemical compound CC1=CC=CC(C)=C1NCCCCNC1=C(C)C=CC=C1C NKPZCZPKVHUSBO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- 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
Definitions
- n is larger than 5 the anesthetic effect is considerably diminished, whereas replacement of the methyl groups by ethyl groups in the 2,6 positions of the aniline rings is also accompanied by diminished anesthetic 'eifect.
- a further requisite for the structures within this system is that the nitrogen atoms have hydrogen groups attached. If these hydrogen atoms are replaced by methyl groups, anesthetic effect is reduced. Of particular significance is the stability of these active agents, with none of the groupings being vulnerable to hydrolysis.
- the compounds were evaluated by the method of Chance and Lobstein, J. Pharmacol, 82, 203 (1944), for determining the median effective dose of a local anesthetic when applied to the cornea of a guinea pig eye.
- a known concentration of solution of the local anesthetic is applied to both eyes of a guinea pig and the eyes kept bathed with this solution for two minutes. The eyes are then blotted to remove excess solution.
- Patent halide suitably Br(CH ),,Br.
- Varying concentrations of the anesthetic agent are used and the percent anesthesia is plotted against concentration. The results are expressed as the ED in mg./ml. which is the quantity of compound per milliliter of solution required to effect 50% anesthesia as established from the plot of concentration vs. percent anesthesia.
- mice The toxicity of the individual compounds was established by administration subcutaneously (s.c.) to mice, in terms of the minimum dose required to be lethal to mice and expressed as LD in milligrams of compound per kilogram of mouse.
- the therapeutic index was then calculated by dividing the LD by the ED the result being a single figure embracing the anesthetic effectiveness of the compound and its inherent toxicity.
- the selected compounds of this invention are bases and are desirably solubilized when used as their salts with strong acids such as hydrochloric, hydrobromic, sulfuric and the like.
- EXAMPLE 1 A mixture of 66.5 g. (0.55 mole) of 2,6-dimethylani1ine and 22.2 g. (0.11 mole) of trimethylene dibromide was heated on the steam bath for 3 hours. When cool, the formed crystals were separated, rinsed with ether, dried and dissolved in 150 ml. of water. The aqueous solution was rendered alkaline by the addition of 6 N sodium hydroxide and the liberated base extracted with three 200-ml. portions of ether. The combined ether extracts were dried (anhydrous magnesium sulfate), filtered, the ether removed and the residue distilled. There was obtained 13.0 g. (50%) of N,N-trimethylene-bis(2,6-dimethylaniline), B.P. 172174 C. (0.2 mm.).
- N,N'-tetramethylene-bis(2,6-dimethylaniline) was obtained as follows: A mixture of 1.52 g. (0.04 mole) of lithium aluminum hydride in 300 ml. of ether was treated With a slurry of 4.65 g. (0.015 mole) of ('y-[2,6-dimethylanilino]-butyr)-2,6-dimethylanilide in 300 ml. of ether. After stirring under reflux for 30 hours and standing for an additional hours, 1.0 ml. of water followed by 1.0 ml. of saturated sodium chloride and 2.25 ml. of 40% sodium hydroxide solution was added.
- a process for inducing anesthesia in a veterinary animal which comprises administering parenterally an effective amount of a compound of the formula CH3 CH3 CH5 CH8 where n is an integer selected from the group consisting of 3 and 5, said compound being in unit dosage form.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
2,993,831 I I POLYALKYLENEBISANILINE ANESTHETHIS Seymour 1.. Shapiro, Hastings on Hudson, and Louis Freedman, Bronxville, N.Y., assignors to US. Vitamin & Pharmaceutical Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed June 18, 1958, Ser. No. 742,752 3 Claims. (Cl. 167- 52) This invention is concerned with certain N,N'-polymethylene bis(2,6-dimethylanilines) which are unusually effective anesthetic agents and with the process for their preparation.
Specifically, we have now found that compounds of the structure 'wherein 11:3-5, are potent anesthetic agents with desirable lack of toxicity.
If n is larger than 5 the anesthetic effect is considerably diminished, whereas replacement of the methyl groups by ethyl groups in the 2,6 positions of the aniline rings is also accompanied by diminished anesthetic 'eifect. A further requisite for the structures within this system is that the nitrogen atoms have hydrogen groups attached. If these hydrogen atoms are replaced by methyl groups, anesthetic effect is reduced. Of particular significance is the stability of these active agents, with none of the groupings being vulnerable to hydrolysis.
The criticality in the structural requirements for pronounced anesthetic activity is manifest from Table I.
The compounds were evaluated by the method of Chance and Lobstein, J. Pharmacol, 82, 203 (1944), for determining the median effective dose of a local anesthetic when applied to the cornea of a guinea pig eye.
A known concentration of solution of the local anesthetic is applied to both eyes of a guinea pig and the eyes kept bathed with this solution for two minutes. The eyes are then blotted to remove excess solution.
Five minutes later, the eyes are tested for the anesthetic effect. A horse hair mounted on a glass rod is used. The hair is pressed against the center of the cornea so that the hair is bent to about the same extent at each application. The hair is applied times to each eye, and the process repeated 5 times for the test (total of 100 prods). The result is reported thus: 100 minus number of blinks=percent anesthesia.
' rates Patent halide, suitably Br(CH ),,Br.
ice
Varying concentrations of the anesthetic agent are used and the percent anesthesia is plotted against concentration. The results are expressed as the ED in mg./ml. which is the quantity of compound per milliliter of solution required to effect 50% anesthesia as established from the plot of concentration vs. percent anesthesia.
The toxicity of the individual compounds was established by administration subcutaneously (s.c.) to mice, in terms of the minimum dose required to be lethal to mice and expressed as LD in milligrams of compound per kilogram of mouse.
The therapeutic index was then calculated by dividing the LD by the ED the result being a single figure embracing the anesthetic effectiveness of the compound and its inherent toxicity.
The selected compounds of this invention are bases and are desirably solubilized when used as their salts with strong acids such as hydrochloric, hydrobromic, sulfuric and the like.
The compounds of the type shown in Formula I where n=3 and 5 are conveniently prepared by the reaction of an excess of 2,6-dimethylaniline with the appropriate The compound where n-=5 has been reported by Sommers et al., J. Am. Chem. Soc., 75, 5280 (1953), with no indication of its utility as an anesthetic agent. However, the attempted preparation of the compound where 11:4 could not be realized by this reaction since even in the presence of an excess of the 2,6-dimethylaniline, the reaction favored was apparently that where the compound cyclized as shown in the equation below.
CH5 CH .l H Br l H Br CH3 CH3 shown in the scheme I below.
The process and compounds of this invention will be more clearly understood from a consideration of the following specific examples which are given for the pur pose of illustration only and are not to be construed as limiting the scope of the invention in any way.
EXAMPLE 1 A mixture of 66.5 g. (0.55 mole) of 2,6-dimethylani1ine and 22.2 g. (0.11 mole) of trimethylene dibromide was heated on the steam bath for 3 hours. When cool, the formed crystals were separated, rinsed with ether, dried and dissolved in 150 ml. of water. The aqueous solution was rendered alkaline by the addition of 6 N sodium hydroxide and the liberated base extracted with three 200-ml. portions of ether. The combined ether extracts were dried (anhydrous magnesium sulfate), filtered, the ether removed and the residue distilled. There was obtained 13.0 g. (50%) of N,N-trimethylene-bis(2,6-dimethylaniline), B.P. 172174 C. (0.2 mm.).
The product crystallized on standing, M.P. 7173 C.
Analysis.-Calcd. for C H N C, 80.8; H, 9.3; N, 9.9. Found: C, 81.1; H, 8.9; N, 10.0.
EXAMPLE 2 A solution of 9.3 g. (0.06 mole) of succinyl chloride in 60 ml. of ether was added gradually with stirring to a solution of 29.0 g. (0.24 mole) of 2,6-dimethylaniline in 200 ml. of ether. After the addition, stirring was continued for 40 minutes and the mixture of product and 2,6- dimethylaniline hydrochloride separated, washed with ether and then with water. The water-insoluble product N,N bis(2,6-dimethylphenyl)succinamide, 24.9 g. (90%), melted at 322-323 C. after recrystallization from methyl Cellosolve.
Analysis.Calcd. for C H N O C, 74.0; H, 7.5; N, 8.6. Found: C, 73.8; H, 6.9; N, 8.7.
There was similarly prepared from 2,6-dimethylaniline and malonyl chloride, N,N'-bis(2,6-dimethylpheuyl) malonarnide, M.P. 266267 C.
Analysis.-Calcd. for C H N O C, 73.5; H, 7.1; N, 9.0. Found: c, 73.1; H, 7.3; N, 8.9.
There was similarly prepared from 2,6-dimethylaniline and adipyl chloride, N,N-bis(2,6-dirnethylphenyl)adipamide, M.P. 290-292 C.
Analysis.-Calcd. for C H N O C, H, N,
7.9. Found: C, 75.1; H, 8.2; N, 8.2.
EXAMPLE 3 the residue separated and rinsed with two 300-m1. portions of ether. The combined filtrates were concentrated to about 25 ml. and on standing at C., 5.9 g. (47.5%) of the product separated, M.P. 145-148 C., recrystallized (heptane) M.P. 149-150" C.
V 4,. q I 4 Analysis.-Calcd. for C H N O: C, 77.4; H, 8.4.
Found: C, 77.5; H, 8.0.
EXAMPLE 4:
N,N'-tetramethylene-bis(2,6-dimethylaniline) was obtained as follows: A mixture of 1.52 g. (0.04 mole) of lithium aluminum hydride in 300 ml. of ether was treated With a slurry of 4.65 g. (0.015 mole) of ('y-[2,6-dimethylanilino]-butyr)-2,6-dimethylanilide in 300 ml. of ether. After stirring under reflux for 30 hours and standing for an additional hours, 1.0 ml. of water followed by 1.0 ml. of saturated sodium chloride and 2.25 ml. of 40% sodium hydroxide solution was added. The formed granular precipitate was separated, rinsed with ether and the combined ether filtrates concentrated. Unreacted anjlide (2.4 g.) precipitated and was separated. The filtrate was evaporated to yield a residue which was distilled. There was obtained 1.11 g. (25%) of product boiling at 172182 C. (0.11 mm.). On standing at room temperature the product crystallized, M.P. 61-63 C., recrystallized (pentane) M.P. 7273 C.
Analysis.Calcd. for C H N C, 81.0; H, 9.5; N, 9.5. Found: C, 81.1; H, 9.4; N, 9.7.
It is to be understood that it is intended to cover all changes and modifications of the examples of the invention herein chosen for the purpose of illustration which do not constitute departure from the spirit and scope of the invention.
We claim:
1. A process for inducing anesthesia in a veterinary animal which comprises administering parenterally an effective amount of a compound of the formula CH3 CH3 CH5 CH8 where n is an integer selected from the group consisting of 3 and 5, said compound being in unit dosage form.
2. The process of claim 1 where n=3. 3. The process of claim 1 where n=5.
References Cited in the file of this patent OTHER REFERENCES Beilstein, vol. 12, 1929, pp. 828, 1110. Chem. Abst., vol. 49, 1955, p. 317 (at c and e).
Claims (1)
1. A PROCESS FOR INDUCING ANESTHESIA IN A VETERINARY ANIMAL WHICH COMPRISES ADMINISTERING PARATERALLY AN EFFECTIVE AMOUNT OF A COMPOUND OF THE FORMULA WHERE N IS AN INTEGER SELECTED FROM THE GROUP CONSISTING OF 3 AND 5, SAID COMPOUND BEING IN UNIT DOSAGE FORM.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US742752A US2993831A (en) | 1958-06-18 | 1958-06-18 | Polyalkylenebisaniline anesthetics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US742752A US2993831A (en) | 1958-06-18 | 1958-06-18 | Polyalkylenebisaniline anesthetics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2993831A true US2993831A (en) | 1961-07-25 |
Family
ID=24986061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US742752A Expired - Lifetime US2993831A (en) | 1958-06-18 | 1958-06-18 | Polyalkylenebisaniline anesthetics |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2993831A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193456A (en) * | 1962-04-16 | 1965-07-06 | Ct Europ De Rech S Mauvernay | 3, 5-dimethoxy-4-allyloxy-benzamide compositions and method of use |
| US3288835A (en) * | 1966-11-29 | Substituted-carbamyl)-alk- oxyj-phenyl acetic acid esters | ||
| US3300532A (en) * | 1959-06-26 | 1967-01-24 | Donau Pharmazie Gmbh | Nu-(beta-diethylamino ethyl)-nu-[beta-hydroxy-beta-(phenyl) ethyl] anilines and salts thereof |
| US3310464A (en) * | 1962-06-06 | 1967-03-21 | Geigy Ag J R | Process for controlling nematodes with n, n'-di(tetra-substituted phenyl) diaminomethanes |
| US3448196A (en) * | 1959-04-15 | 1969-06-03 | Centre Nat Rech Scient | Method and composition for inducing local anesthesia with mono-(beta-diethylaminoethyl)amide of parachlorophenoxyacetic acid |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2311754A (en) * | 1939-05-22 | 1943-02-23 | Ici Ltd | Manufacture of anilides |
| US2311753A (en) * | 1939-05-17 | 1943-02-23 | Ici Ltd | Manufacture of new anilides |
| US2499352A (en) * | 1948-01-02 | 1950-03-07 | Wyeth Corp | Substituted glycinamides |
| US2528267A (en) * | 1950-10-31 | Eobeet j | ||
| US2669582A (en) * | 1952-04-05 | 1954-02-16 | Searle & Co | Basically substituted amides of dicarboxylic acids |
| US2739981A (en) * | 1952-08-26 | 1956-03-27 | American Home Prod | Diamines and salts thereof |
| US2744929A (en) * | 1952-09-26 | 1956-05-08 | Shell Dev | Production of unsaturated carboxylic acids |
| US2824041A (en) * | 1952-10-28 | 1958-02-18 | Pfizer & Co C | Process of inducing hypnosis by unsaturated tertiary carbinols |
-
1958
- 1958-06-18 US US742752A patent/US2993831A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528267A (en) * | 1950-10-31 | Eobeet j | ||
| US2311753A (en) * | 1939-05-17 | 1943-02-23 | Ici Ltd | Manufacture of new anilides |
| US2311754A (en) * | 1939-05-22 | 1943-02-23 | Ici Ltd | Manufacture of anilides |
| US2499352A (en) * | 1948-01-02 | 1950-03-07 | Wyeth Corp | Substituted glycinamides |
| US2669582A (en) * | 1952-04-05 | 1954-02-16 | Searle & Co | Basically substituted amides of dicarboxylic acids |
| US2739981A (en) * | 1952-08-26 | 1956-03-27 | American Home Prod | Diamines and salts thereof |
| US2744929A (en) * | 1952-09-26 | 1956-05-08 | Shell Dev | Production of unsaturated carboxylic acids |
| US2824041A (en) * | 1952-10-28 | 1958-02-18 | Pfizer & Co C | Process of inducing hypnosis by unsaturated tertiary carbinols |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3288835A (en) * | 1966-11-29 | Substituted-carbamyl)-alk- oxyj-phenyl acetic acid esters | ||
| US3448196A (en) * | 1959-04-15 | 1969-06-03 | Centre Nat Rech Scient | Method and composition for inducing local anesthesia with mono-(beta-diethylaminoethyl)amide of parachlorophenoxyacetic acid |
| US3300532A (en) * | 1959-06-26 | 1967-01-24 | Donau Pharmazie Gmbh | Nu-(beta-diethylamino ethyl)-nu-[beta-hydroxy-beta-(phenyl) ethyl] anilines and salts thereof |
| US3193456A (en) * | 1962-04-16 | 1965-07-06 | Ct Europ De Rech S Mauvernay | 3, 5-dimethoxy-4-allyloxy-benzamide compositions and method of use |
| US3310464A (en) * | 1962-06-06 | 1967-03-21 | Geigy Ag J R | Process for controlling nematodes with n, n'-di(tetra-substituted phenyl) diaminomethanes |
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