US4193926A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-(Polyalkoxy phenyl)-2-pyrrolidones
Assignee: Bayer Pharma AG
•
Filing: 1976-02-18
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Granted: 1980-03-18
•
Expires: 1996-02-18
Abstract
Abstract 4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R 1 and R 2 each are hydrocarbon of up to 18 carbon atoms at least one being other than methyl, a heterocyclic ring, or alkyl of 1-5 carbon atoms substituted by halogen, OH, COOH, alkoxy, alkoxycarbonyl or an amino group; R' is H, alkyl, aryl or acyl; and X is O or S; possess neuropsychotropic activity. The compounds wherein X is O can be produced by saponifying and decarboxylating a corresponding 2-pyrrolidone-3-carboxylic acid alkyl ester or cyclizing a corresponding 3-phenyl-4-amino-butyric acid or alkyl ester thereof. The pyrrolidones can be converted to the corresponding thiopyrrolidones by reaction with phosphorous pentasulfide in the presence of base.
Inventors
- 👤 Ralph Schmiechen
- 👤 Reinhard Horowski
- 👤 Dieter Palenschat
- 👤 Gert Paschelke
- 👤 Helmut Wachtel
- 👤 Wolfgang Kehr
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 11:45
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
53 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR49## selected from the group consisting of 4-(3-ethoxy-4-metoxyphenyl)-2-pyrrolidone; 4-(3-propoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-butoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-hexyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isopropoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(1-methylpropoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isobutoxy-4-methoxyphenyl)-2-pyrrolidione; 4-(3-allyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-methyl-2-butenyloxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methoxymethoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-hydroxyethoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2,2,2-trifluoroethoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-benzyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-phenoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methoxy-4-ethoxyphenyl)-2-pyrrolidone; 4-(3-methoxy-4-butoxyphenyl)-2-pyrrolidone; 1-acetyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidone; 4-(3-decyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-83-octadecyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-methylbutyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-neopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-propinyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyanomethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclobutoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclohexyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-tetrahydrothienyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-tetrahydrofuryl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopropylmethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopentylmethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methallyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(4-propinyloxy-3-methoxyphenyl)-2-pyrrolidone; 4-(4-cyclopentyloxy-3-methoxyphenyl)-2-pyrrolidone; 4-(3,4-diethoxyphenyl)-2-pyrrolidone; 4-(3,4-diisobutoxyphenyl)-2-pyrrolidone; 4-(3-isobutoxy-4-methoxyphenyl)-pyrrolidine-2-thione; 4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidine-2-thione; and 4-(3-(2-tetrahydrofuryloxy)-4-methoxyphenyl)-2-pyrrolidone.
Claim 2
Dependent Claim
53 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR49## selected from the group consisting of 4-(3-ethoxy-4-metoxyphenyl)-2-pyrrolidone; 4-(3-propoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-butoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-hexyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isopropoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(1-methylpropoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isobutoxy-4-methoxyphenyl)-2-pyrrolidione; 4-(3-allyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-methyl-2-butenyloxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methoxymethoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-hydroxyethoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2,2,2-trifluoroethoxy)-4-methoxyphenyl)-2-pyrrolidone; 4-(3-benzyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-phenoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methoxy-4-ethoxyphenyl)-2-pyrrolidone; 4-(3-methoxy-4-butoxyphenyl)-2-pyrrolidone; 1-acetyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidone; 4-(3-decyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-83-octadecyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-methylbutyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-neopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-isopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-propinyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyanomethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclobutoxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclohexyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(2-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-tetrahydrothienyl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-(3-tetrahydrofuryl)-oxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopropylmethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-cyclopentylmethyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(3-methallyloxy-4-methoxyphenyl)-2-pyrrolidone; 4-(4-propinyloxy-3-methoxyphenyl)-2-pyrrolidone; 4-(4-cyclopentyloxy-3-methoxyphenyl)-2-pyrrolidone; 4-(3,4-diethoxyphenyl)-2-pyrrolidone; 4-(3,4-diisobutoxyphenyl)-2-pyrrolidone; 4-(3-isobutoxy-4-methoxyphenyl)-pyrrolidine-2-thione; 4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidine-2-thione; and 4-(3-(2-tetrahydrofuryloxy)-4-methoxyphenyl)-2-pyrrolidone.
Claim 3
Dependent Claim
6 words
The compound of claim 1, 4-(3,4-diisobutoxyphenyl)-2-pyrrolidone.
Claim 4
Dependent Claim
6 words
The compound of claim 1, 4-(3-isobutoxy-4-methoxyphenyl)-pyrrolidine-2-thione.
Claim 5
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidine-2-thione.
Claim 6
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2-tetrahydrofuryloxy]-4-methoxyphenyl)-2-pyrrolidone.
Claim 7
Dependent Claim
56 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR50## wherein R 1 is methyl; R 2 is cycloalkyl or cycloalkylalkyl of 3-7 carbon atoms; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
Claim 8
Dependent Claim
56 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR50## wherein R 1 is methyl; R 2 is cycloalkyl or cycloalkylalkyl of 3-7 carbon atoms; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
Claim 9
Dependent Claim
6 words
The compound of claim 1, 4-(3-ethoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 10
Dependent Claim
6 words
The compound of claim 1, 4-(3-propoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 11
Dependent Claim
6 words
The compound of claim 1, 4-(3-butoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 12
Dependent Claim
6 words
The compound of claim 1, 4-(3-hexyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 13
Dependent Claim
6 words
The compound of claim 1, 4-(3-isopropoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 14
Dependent Claim
6 words
The compound of claim 1, 4-83-[1-methypropoxy]-4-methoxyphenyl)-2-pyrrolidone.
Claim 15
Dependent Claim
6 words
The compound of claim 1, 4-(3-isobutoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 16
Dependent Claim
6 words
The compound of claim 1, 4-(3-allyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 17
Dependent Claim
6 words
The compound of claim 1, 4-83-[3-methyl-2-butenyloxy]-4-methoxyphenyl)-2-pyrrolidone.
Claim 18
Dependent Claim
6 words
The compound of claim 1, 4-(3-methoxymethoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 19
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2-hydroxyethoxy]-4-methoxyphenyl)-2-pyrrolidone.
Claim 20
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2,2,2-trifluoroethoxy]-4-methoxyphenyl)-2-pyrrolidone.
Claim 21
Dependent Claim
6 words
The compound of claim 1, 4-(3-benzyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 22
Dependent Claim
6 words
The compound of claim 1, 4-(3-phenoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 23
Dependent Claim
6 words
The compound of claim 1, 4-(3-methoxy-4-ethoxyphenyl)-2-pyrrolidone.
Claim 24
Dependent Claim
6 words
The compound of claim 1, 4-(3-methoxy-4-butoxyphenyl)-2-pyrrolidone.
Claim 25
Dependent Claim
6 words
The compound of claim 1, 1-acetyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidone.
Claim 26
Dependent Claim
59 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR51## wherein one of R 1 and R 2 is methyl and the other is mono-, di- or trihaloalkyl; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
Claim 27
Dependent Claim
59 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR51## wherein one of R 1 and R 2 is methyl and the other is mono-, di- or trihaloalkyl; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
Claim 28
Dependent Claim
6 words
The compound of claim 1, 4-(3-decyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 29
Dependent Claim
6 words
The compound of claim 1, 4-(3-octadecyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 30
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2-methylbutyl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 31
Dependent Claim
6 words
The compound of claim 1, 4-(3-neopentyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 32
Dependent Claim
6 words
The compound of claim 1, 4-(3-isopentyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 33
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2-propinyl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 34
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyanomethyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 35
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclobutoxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 36
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 37
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclohexyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 38
Dependent Claim
6 words
The compound of claim 1, 4-(3-[3-methylcyclopentyl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 39
Dependent Claim
6 words
The compound of claim 1, 4-(3-[2-methylcyclopentyl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 40
Dependent Claim
6 words
The compound of claim 1, 4-(3-[3-tetrahydrothienyl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 41
Dependent Claim
6 words
The compound of claim 1, 4-(3-[3-tetrahydrofuryl]-oxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 42
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclopropylmethyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 43
Dependent Claim
6 words
The compound of claim 1, 4-(3-cyclopentylmethyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 44
Dependent Claim
6 words
The compound of claim 1, 4-(3-methallyloxy-4-methoxyphenyl)-2-pyrrolidone.
Claim 45
Dependent Claim
6 words
The compound of claim 1, 4-(4-propinyloxy-3-methoxyphenyl)-2-pyrrolidone.
Claim 46
Dependent Claim
6 words
The compound of claim 1, 4-(4-cyclopentyloxy-3-methoxyphenyl)-2-pyrrolidone.
Claim 47
Dependent Claim
6 words
The compound of claim 1, 4-(3,4-diethoxyphenyl)-2-pyrrolidone.
Claim 48
Dependent Claim
58 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR52## wherein one of R 1 and R 2 is methyl and the other is tetrahydrothienyl or tetrahydrofuryl; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
Claim 49
Dependent Claim
58 words
4-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR52## wherein one of R 1 and R 2 is methyl and the other is tetrahydrothienyl or tetrahydrofuryl; R' is a hydrogen atom, alkyl of 1-5 carbon atoms, hydrocarbon aryl or aralkyl of up to 10 carbon atoms or alkanoyl of 1-6 carbon atoms; and X is an oxygen atom or a sulfur atom.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-03-18 | 1983-09-17 | 1984-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-03-18 | 1987-09-17 | 1988-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-03-18 | 1991-09-17 | 1992-03-18 | $7700.00 | Window Closed / Lapsed |