前苏联专利SU1373318A3 Method of producing pyrrolidinone derivatives or acid-additive salts thereof

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专利摘要:
Die Erfindung betrifft neue 1-Benzyl-4-aminoalkyl- pyrrolidin-2-one der allgemeinen Formel worin R, Wasserstoff oder einen Alkylrest, R2 einen Phenylrest, der ein- oder zweifach durch Alkoxy, Fluor, Chlor, Brom, Trifluormethyl, Alkyl, Hydroxy oder nitro substituiert sein kann oder einen Pyridylrest und R3 und R4, die gleich oder verschieden sein können, Wasserstoff oder einen Alkylrest bedeuten oder beide Reste R3 and R4 zusammen mit dem Stickstoffatom einen gesättigten 5- oder 6-Ring, der als weiteres Heteroatom ein 0- oder N-Atom enthalten und gegebenenfalls durch Methyl substituiert sein kann oder einen Imidazolring bilden und wobei die Aminoalkylgruppe in 4- oder 5-Stellung steht und deren Säureadditionssalze. Die neuen verbindungen haben sich im Tierversuch als wirksam bei der Verminderung beziehungsweise Aufhebung von Zustandsformen eingeschränkter cerebraler Leistungsfähigkeit erwiesen.
公开号:SU1373318A3
申请号:SU843796136
申请日:1984-10-03
公开日:1988-02-07
发明作者:Вебер Карл-Гейнц；Вальтер Герхард；Шнейдер Клаус；Гинцен Дитер；Иозеф Кун Франц；Лер Эрих
申请人:Берингер Ингельгейм Кг (Фирма)；
IPC主号:

专利说明:

1137331
The invention relates to the field of production of new pyrrolidinone derivatives of the general formula
CH1

w RI
where R, is phenyl unsubstituted or substituted by fluorine, mono- or dichloro; RJ is hydrogen; RJ - C, - Cj-alkyl;
or R1
and Ra are the same and mean lower alkyl or together with the nitrogen atom form a morpholine or N-methylpiperazine ring, with the aminoalkyl-group in position 4 or 5,
or their acid-a, edible salts, which can be used as a nootropic agent.
The purpose of the invention is to develop, on the basis of known methods, a method for the preparation of new compounds possessing valuable pharmacological properties with increased biological activity with low toxicity.
Example 1. 1-Benzyl-4 di-ethyl aminomethyl-pyrrolidin-2-one.
14 g (0.06 mol) of crude 1-benzyl-4-chloromethyl-pyrrolidin-2-one, 10 g of diethylamine and 50 ml of dimethylformamide are stirred for 2 hours in an autoclave at 150 ° C. It is then evaporated to dryness in vacuo, the residue is taken up in methylene chloride, washed with water and then extracted twice with 25 ml of 2N HC1. The aqueous phase is separated, made alkaline with caustic soda, and the organic base is extracted by shaking with methylene chloride. The chloromethylene phase is evaporated and the residue obtained is subjected to vacuum distillation.
Yield 10 g (61% of theoretical yield) with a boiling point of 155-158 ° C.
EXAMPLE 2. 1- (4-Fluoro-benzyl) 4-N-methyl-piperazine-methyl-pyropoly-DIN-2-OH.
0
-jr
20
25
zo
35
40 45 50
55
82
5 g (0.002 mol) of 1- (4-fluorobenzyl) -A-chloromethyl-pyrrolidin-2-one and 4.4 g (0.04 mol) of 1-methyl piperazine in 30 ml of dimethylformamide are boiled with reverse a refrigerator for 2 hours. Then most of the dimethylformamide is distilled off in vacuum, the residue is taken up in methylene chloride, washed with water, the organic phase is dried and then evaporated again. The residue is chromatographed on Sin using a mixture of methylene chloride and methanol (95: 5) as eluent. The main fraction was evaporated and the residue (5 g) was dissolved in 30 ml of methanol. To the resulting solution was added 2.8 g of fumic acid. 5.2 g (48%) of the theoretical yield of the indicated compound are isolated as crystalline fumarate. M.p. 179-180 ° C.
The 4-chloromethyl compound used as the raw material was prepared as follows.
24 g (0.11 mol) of 1- (4-fluoro-benzyl) -4-hydroxymethyl-pyrrolidin-2-one with 10 ml (0.14 mol) of thionyl chloride is refluxed in 200 ml of chloride methylene first for 10 hours and then, after adding additional IO ml of thionyl chloride, for another 6 hours. While cooling with ice, it is neutralized with ammonia and, after separation, the organic phase is dried and evaporated. 23 g of residue (92% of theoretical yield) are obtained in the form of a red-brown oil.
EXAMPLE 3. 1- (4-Fluorobenzyl) -4-morpholinomethyl-pyrrolidin-2-one.
6.7 g (0.023 mol) of 1- (4-fluoro-benzyl) 4-hydroxymethyl-pyrrolidin-2-one methanesulfonic ester and 2.6 g (0.03 mol) of morpholine in 20 ml of dioxane are boiled with reflux for 2 hours. The solvent is then evaporated in vacuo, the residue is taken up in methylene chloride and extracted with 50 ml of 2N. hydrochloric acid. The aqueous extracts are basified with ammonia and the resulting oily base is shaken with methylene chloride. The chloromethylene phase is dried and evaporated. The resulting residue is taken up in 30 ml of methanol and 1.2 g of fumaric acid is added in a warm condition. After cooling, fumarate of the above compound precipitated as crystals.
313733
Output: 7 g (57% of theoretical yield) of colorless crystals with so pl. 175-176 ° C.
The ester used as starting material from the compound is prepared as follows.
To 8.9 g (0.04 mol) of 1- (4-fluorobenz1) -4-about xymethyl-pyrrolidin-2-one in 100 ml of absolute methylene chloride, and 4.8 g of pyridine, 6, 9 g
(0.06 mol) of methanesulfonic acid chloride. The mixture is heated under reflux for 2.5 hours, cooled and shaken with a mixture of dilute ammonia and water. The organic phase is dried and evaporated. Obtain 1I g (93% of theoretical yield) of ester with so pl. 84-86 ° C.
Analogously to examples 1-3 get the target products listed in table 1.
Sleep
-N

-Sh-CH (CH j)
PRI me R 8. 1-Benzyl-5-dimethyl-aminomethyl-pyrrolidin-2-one.
8.5 g (0.03 mol) of 1-benzyl-5-hydroxymethyl-pyrrolidin-2-one methanesulfonic acid ester together with a solution of 10 g of dimethylamine in 60 ml of dioxane is heated in an autoclave for 3 hours to 150 ° C. The cooled reaction mixture in vacuo is concentrated to a vacuum. The residue is dissolved in 2N. hydrochloric acid and extracted with ether. The acidic aqueous phase is made alkaline with concentrated ammonia and extracted by shaking with methylene chloride. Chloris solution
Table 1
A - CH2
ABOUT
Output,% of theory
T.kip.005 5 (base)
86
Bp 175 (base)
90
In addition, methylene is dried and evaporated. The residue (6.5 g) with an equivalent amount of fumaric acid is converted to the acid fumarate of the indicated compound. Yield: 6.4 g (61% of theoretical yield); m.p. 137-138 C.
Used as a starting product, the compound was prepared as follows.
To a solution of iO, 26 g (0.05 mol) of 1-benzyl-5-oximesh1-pyrrolidin-2-one and 5.6 g (0.055 mol) of triethylamine in 80 ml of methylene chloride was added 6.3 g (0.055 mol) methanesulfonic acid chloride in 20 ml of methylene chloride. The reaction mixture is then heated under reflux for 1 hour and, after cooling, extracted by shaking with water. After drying over anhydrous sodium sulfate, the organic phase
ja
- -N I
CHn
ABOUT
Example
R,
R.-N (C, Hj) jН
ten
, n
eleven
-NCCH,)
H
12-N (CjH5), H
13
-N (CH) j
H
14
-N (CjH5) iH
/
PRI me R 15. I-Benzyl-4-dimethylaminomethyl-pyrrolidin-2-one.
68 g (0.24 mol) of 1-benzyl-4-hydroxymethyl-pyrrolidin-2-one methylsulfonic ester is dissolved in 500 ml of dioxane and reacted with 100 g of dimethylamine at 150 ° C for 3 hours. The mixture is then absorbed in 500 ml of methylene chloride and shake with 100 ml of water. The organic phase is separated, dried and the solvent is evaporated. The residue is mixed with 50 ml of alcoholic hydrochloric acid and the hydrochloride of the above compound is precipitated by the addition of ether.
evaporated in a rotary evaporator. 14.1 g of the mesylate are obtained in the form of a yellow oil.
Analogously to Example 8, the compounds listed in Table 2 are prepared.
table 2
Mp ° C / bp °
Output,% of theory
163-164 (hydrochloride) 65
258 (dihydrochloride)
157-158 (fumarate)
149-151 (hydrochloride) 68
167-168 (fumarate)
62
159-161 (hydrochloride) 60
Receive 33.7 g (52% of theoretical yield) with T. pl, 175 ° C.
The results of pharmacological experiments.
For the study of the elimination effect of scopolamine-dementia dacha, rats were used as experimental animals, who were trained to rescue themselves in a cage onto a platform when 80% of the animals received current impulses through the floor grid after a while that they were safe on the platform. When animals give scopolamine (0.6 mg / kg intravenously), then in 80% of rats, it is possible to establish a retrogenic effect on
short-term memory, i.e. the animals forget that they are safe on the platform.
A substance that is able to counteract cerebral insufficiency can eliminate this action. After giving scopolamine animals give
Compound
1- (4-Fluorobenzyl) -4-K-methylpiperazinyl-methyl-pyrrolidin-2-OH
I-Benzyl-4-diethylaminomethyl-pyrrolidin-2-one
1- (3,4-Dichlorobenzyl) -5-diethylaminomethyl-pyrrolidin-2-o
1- {4-Fluorobenzyl) -4-morpholino-methyl-pyrrolidin-2-one
Piracetam (known)
The data of Table 3 indicate a higher activity of new compounds compared to the lime structural analogue.
The novel pyrrolidinone derivatives are not toxic.

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining pyrrolidinone derivatives of the general formula
) -SNg 0
-N /
CH2 RI
phenyl, unsubstituted or substituted by fluorine, mono- or dichlor; hydrogen; C, -C} -alkyl;
are the same and mean lower alkyl or together with
g
33I8
test substance and determine how many percent of the animals did not lose the short-term memory after scopolamine was given. Table 3 shows the dose of the investigated substances, eliminating, on average, 50% of animals with dementia caused by scopolamine.
Table 3
Dose, administered by mouth, mg / kg
a nitrogen atom forms a morpholine or N-methylpiperizin ring, with an amino-alkyl group having the position 4 or 5 or their acid addition salts, characterized in that the compound of the general formula
X-CH2
0
CH2
RI
where R has the indicated value; X is a halogen atom or a mesyloxy radical,
subjected to interaction with the compound of the general formula NH 3
where R and RJ have the indicated meanings, followed by isolating the desired product in free form or as an acid addition salt.

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法律状态:

优先权:

申请号 | 申请日 | 专利标题

DE19833336024|DE3336024A1|1983-10-04|1983-10-04|4-AMINO-L-BENZYL-PYRROLIDINONE AND ITS ACID ADDITION SALTS, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS|

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