US4094992A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Benzylidene derivatives
Assignee: Synthelabo SA
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Filing: 1976-07-16
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Granted: 1978-06-13
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Expires: 1996-07-16
Abstract
Abstract Compounds of the formula: ##STR1## in which X 1 , X 2 and X 3 , which are identical or different each represent hydrogen, halogen, methyl, or methoxy, n represents an integer from 1 to 10, and R represents hydroxyl, OM, NH 2 , NH(CH 2 ) 3 --COH, --NH(CH 2 ) 3 --COOM, (where M represents an alkali metal atom), NH(CH 2 ) 3 --COOC 2 H 5 , NH-cycloalkyl, NH-phenyl, NH-benzyl (where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl), NH-alkyl, N(alkyl) 2 and N-(alkyl)-(benzyl), the aforesaid alkyls being straight or branched and having from 1 to 4 carbon atoms and the aforesaid cycloalkyls having from 3 to 6 carbon atoms, except that when X 1 and X 3 are both hydrogen, n is 1 and R is OH, X 2 is not chlorine in the 5-position are useful in the treatment of epilepsy by oral or parenteral administration.
Inventors
- 👤 Jean-Pierre Kaplan
- 👤 Maurice Jalfre
- 👤 Don Pierre Rene Lucien Giudicelli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 08:50
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/02; C07C251/04; C07C251/10; C07C251/16; A; A61; A61K; A61K31/00; A61K31/16; A61K31/185; A61K31/19; A61K31/195; A61K31/197; C07C229/00; C07C229/02; C07C229/04; C07C229/06; C07C229/10; C07C237/00; C07C237/02; C07C237/04; C07C237/06; C07C249/00; C07C249/02
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
79 words
Compound of claim 1 ##STR24## in which one of X 1 and X 3 is halogen, methyl, or methoxy, and X 2 and the other of X 1 and X 3 are each independently hydrogen, halogen, methyl or methoxy, n represents an integer from 1 to 10, and R is NH 2 , NH-(C 3-6 cycloalkyl), NH-phenyl, NH-benzyl, NH-(C 1-4 alkyl), N-(C 1-4 alkyl) 2 or N-(C 1-4 alkyl)-(benzyl), where each benzyl may be substituted by halogen and/or trifluoromethyl.
Claim 2
Dependent Claim
24 words
A compound according to claim 1 in which one or more of X 1 , X 2 and X 3 is chlorine or bromine.
Claim 3
Dependent Claim
13 words
A compound according to claim 1, in which R is NH 2 .
Claim 4
Dependent Claim
33 words
A compound ##STR25## wherein each of X 1 , X 2 and X 3 is independently selected from hydrogen, chlorine, fluorine, methyl or methoxy and n is an integer of 1 to 10.
Claim 5
Dependent Claim
33 words
A compound ##STR25## wherein each of X 1 , X 2 and X 3 is independently selected from hydrogen, chlorine, fluorine, methyl or methoxy and n is an integer of 1 to 10.
Claim 6
Dependent Claim
25 words
A compound according to claim 4, in which X 1 is a substituent in the 4- or 5-position and X 2 is a hydrogen atom.
Claim 7
Dependent Claim
9 words
A compound according to claim 5 which is 4-N-[α-(4-chlorophenyl)-5-fluoro-2-hydroxy-benzylidenyl]-amino-butyramide.
Claim 8
Dependent Claim
65 words
Compound of claim 1 of the formula: ##STR26## in which one of X 1 and X 3 is halogen, methyl, or methoxy, and X 2 and the other of X 1 and X 3 are each independently hydrogen, halogen, methyl or methoxy, n represents an integer from 1 to 10, and R represents NH 2 , NH--(C 1-4 alkyl), or N(C 1-4 alkyl) 2 .
Claim 9
Dependent Claim
56 words
Compound of claim 1 of the formula: ##STR27## in which one of X 1 and X 3 is halogen, methyl, or methoxy, and X 2 and the other of X 1 and X 3 are each independently hydrogen, halogen, methyl or methoxy, n represents an integer from 1 to 10, and R represents NH-(C 3-6 cycloalkyl).
Claim 10
Dependent Claim
71 words
Compound of claim 1 of the formula: ##STR28## in which one of X 1 and X 3 is halogen, methyl, or methoxy, and X 2 and the other of X 1 and X 3 are each independently hydrogen, halogen, methyl or methoxy, n represents an integer from 1 to 10, and R represents NH-phenyl, NH-benzyl, or N-(C 1-4 alkyl)-(benzyl) where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl.
Claim 11
Dependent Claim
9 words
A compound according to claim 5 which is 4-N-[α-phenyl-5-fluoro-2-hydroxy-benzylidenyl]-amino-butyramide.
Claim 12
Dependent Claim
9 words
A compound according to claim 5 which is N-(4-fluorobenzyl)-4-N-[α-phenyl-5-fluoro-2-hydroxy-benzylidenyl]-amino-butyramide.
Claim 13
Dependent Claim
38 words
A pharmaceutical composition suitable for the treatment of epilepsy comprising, as an active ingredient, an amount of a compound of claim 1 effective for treating epilepsy in association with a significant amount of a compatible pharmaceutically acceptable excipient.
Claim 14
Dependent Claim
28 words
A method of treating epilepsy which comprises administering to a subject liable to epilepsy an effective amount of a compound of claim 1 sufficient to relieve said epilepsy.
References Cited (Backward Citations)
US3371085A
Cited
US3429874A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-12 | 1981-12-12 | 1982-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-12 | 1985-12-12 | 1986-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-12 | 1989-12-12 | 1990-06-13 | $7700.00 | Window Closed / Lapsed |