US4855320A
Expired / Lapsed
US
⏱️ 0.0 years remaining
5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processes for the preparation thereof and medicaments containing them
Assignee: Dr Willmar Schwabe GmbH and Co KG
•
Filing: 1987-05-04
•
Granted: 1989-08-08
•
Expires: 2007-05-04
Abstract
Abstract The present invention provides 5-arylalkyl-4-alkoxy-2(5H)-furanones of the formula: <IMAGE> (I) wherein the oxygen atoms on C-5 and C- alpha , relative to one another, are in the threo-position, with the exclusion of those compounds of the formula (I) wherein R2 is H or CH3 when n=0 or 2, Ro=H, R1=CH3, R3=H and R4=H. The present invention also provides processes for their preparation, as well as new 3-alkoxy-5-(subst.)-phenyl-2(E), 4(E)-pentadienoates as reactive intermediates for the preparation of the new furanone derivatives. The new furanone derivatives of the threo series are active as anticonvulsives/anti-epileptics. Therefore, the present invention also provides medicaments which contain these new furanone derivatives, as well as known furanones, the anticonvulsive/anti-epileptic effectiveness of which has been found for the first time.
Inventors
- 👤 Shyam S. Chatterjee
- 👤 Klaus Klessing
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:59
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/40; C07C59/58; C07C59/64; A; A61; A61P; A61P25/00; A61P25/08; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/60
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
193 words
5-Arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR18## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein n is 0, 1 or 2, R o is a hydrogen atom or an alkyl radical containing up to 3 carbon atoms, R 1 a straight-chained or branched alkyl radical containing up to 5 carbon atoms, R 2 is a hydrogen atom, an alkyl radical containing up to 3 carbon atoms or the radical ##STR19## wherein R 5 is an alkyl radical containing up to 5 carbon atoms or an ethoxyethyl or methoxyethyl radical and R 6 is a hydrogen atom, an alkyl radical containing up to 5 carbon atoms or a methoxymethyl radical, R 3 and R 4 , independently of one another, are hydrogen, fluorine, chlorine or bromine atoms, alkyl radicals containing up to 3 carbon atoms, perfluoroalkyl radicals containing up to 3 carbon atoms, a difluoromethoxy radical or a nitro group, with the exclusion of those compounds of formula (I) wherein R 2 is H or CH 3 when n=0 or 2, R o =H, R 1 =CH 3 , R 3 =H and R 4 =H.
Claim 2
Dependent Claim
193 words
5-Arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR18## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein n is 0, 1 or 2, R o is a hydrogen atom or an alkyl radical containing up to 3 carbon atoms, R 1 a straight-chained or branched alkyl radical containing up to 5 carbon atoms, R 2 is a hydrogen atom, an alkyl radical containing up to 3 carbon atoms or the radical ##STR19## wherein R 5 is an alkyl radical containing up to 5 carbon atoms or an ethoxyethyl or methoxyethyl radical and R 6 is a hydrogen atom, an alkyl radical containing up to 5 carbon atoms or a methoxymethyl radical, R 3 and R 4 , independently of one another, are hydrogen, fluorine, chlorine or bromine atoms, alkyl radicals containing up to 3 carbon atoms, perfluoroalkyl radicals containing up to 3 carbon atoms, a difluoromethoxy radical or a nitro group, with the exclusion of those compounds of formula (I) wherein R 2 is H or CH 3 when n=0 or 2, R o =H, R 1 =CH 3 , R 3 =H and R 4 =H.
Claim 3
Dependent Claim
61 words
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula: ##STR20## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein one of the two symbols R 3 and R 4 signifies a hydrogen atom and the other a fluorine, chlorine or bromine atom present in the 2'-position or a methyl, trifluoromethyl or nitro group present in the 2'-position.
Claim 4
Dependent Claim
61 words
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula: ##STR20## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein one of the two symbols R 3 and R 4 signifies a hydrogen atom and the other a fluorine, chlorine or bromine atom present in the 2'-position or a methyl, trifluoromethyl or nitro group present in the 2'-position.
Claim 5
Dependent Claim
72 words
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula (II), wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein one of the two symbols R 3 and R 4 signifies a fluorine, chlorine or bromine atom or a trifluoromethyl radical, in each case in the 2'-position, and the other signifies a chlorine or bromine atom or a trifluoromethyl radical, in each case in the 4'-, 5'- or 6'-position.
Claim 6
Dependent Claim
72 words
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula (II), wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein one of the two symbols R 3 and R 4 signifies a fluorine, chlorine or bromine atom or a trifluoromethyl radical, in each case in the 2'-position, and the other signifies a chlorine or bromine atom or a trifluoromethyl radical, in each case in the 4'-, 5'- or 6'-position.
Claim 7
Dependent Claim
57 words
4-Methoxy-5-[methoxy-(phenyl)-methyl]-2(5H)-furanones of the formula: ##STR21## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein R 3 and R 4 have the same meanings as in claim 1, with the exclusion of those compounds of the formula (III) wherein both symbols R 3 and R 4 represent hydrogen atoms.
Claim 8
Dependent Claim
47 words
4-Methoxy-5-phenylmethyl-2(5H)-furanones of the formula: ##STR22## wherein the oxygen atoms on C-5 and C-α, relative to one another, are in the threo-position and wherein R 5 is a methyl or methoxyethyl radical and R 3 , R 4 and R 6 have the meanings given in claim 1.
Claim 9
Dependent Claim
1 words
threo-5-(2'-Chlorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 10
Dependent Claim
1 words
threo-5-(2'-Chlorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 11
Dependent Claim
1 words
threo-5-(2'-Bromophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 12
Dependent Claim
1 words
threo-5-(2'-Bromophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 13
Dependent Claim
1 words
threo-5-(2'-Fluorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 14
Dependent Claim
1 words
threo-5-(2'-Fluorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 15
Dependent Claim
1 words
threo-5-(2'-Trifluoromethylphenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 16
Dependent Claim
1 words
threo-5-(2'-Trifluoromethylphenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
Claim 17
Dependent Claim
1 words
threo-5-(2',5'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
Claim 18
Dependent Claim
1 words
threo-5-(2',5'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
Claim 19
Dependent Claim
1 words
threo-5-(2',4'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
Claim 20
Dependent Claim
1 words
threo-5-(2',4'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
Claim 21
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-chlorophenyl)-methyl]-2(5H)-furanone.
Claim 22
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-chlorophenyl)-methyl]-2(5H)-furanone.
Claim 23
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-bromophenyl)-methyl]-2(5H)-furanone.
Claim 24
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-bromophenyl)-methyl]-2(5H)-furanone.
Claim 25
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-fluorophenyl)-methyl]-2(5H)-furanone.
Claim 26
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-fluorophenyl)-methyl]-2(5H)-furanone.
Claim 27
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-trifluoromethylphenyl)-methyl]-2(5H)-furanone.
Claim 28
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxymethoxy-(2'-trifluoromethylphenyl)-methyl]-2(5H)-furanone.
Claim 29
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxy-(2'-chlorophenyl)-methyl]-2(5H)-furanone.
Claim 30
Dependent Claim
1 words
threo-4-Methoxy-5-[methoxy-(2'-chlorophenyl)-methyl]-2(5H)-furanone.
Claim 31
Dependent Claim
59 words
A pharmaceutical composition containing at least one compound of the formula I as claimed in claim 1, with the exclusion of those compounds of said formula I wherein R 2 is H or CH 3 when n=0 or 2, R 0 =H, R 1 =CH 3 , R 3 =H and R 4 =H, and a pharmacologically inert excipient.
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) | 1992-08-07 | 1993-02-06 | 1993-08-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-08-07 | 1997-02-06 | 1997-08-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-08-07 | 2001-02-06 | 2001-08-08 | $7700.00 | Window Closed / Lapsed |