US4435425A
Expired / Lapsed
US
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Fluorinated diaminobutane derivatives
Assignee: Merrell Toraude et Cie
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Filing: 1981-08-21
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Granted: 1984-03-06
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Expires: 2001-08-21
Abstract
Abstract Fluorinated diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: R 1 represents hydrogen, C 1 -C 6 alkyl, or phenyl-(C 1 -C 4 alkyl); R 2 represents hydrogen, C 1 -C 6 alkyl, phenyl-(C 1 -C 4 alkyl), or R 4 , where R 4 is as defined below; R 3 represents hydrogen, or, except when R 2 represents R 4 , R 4 , where R 4 is as defined below; each R 4 , independently, represents C 2 -C 5 alkylcarbonyl, phenylcarbonyl, phenyl-(C 1 -C 4 alkyl) carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of an L-aminocarboxylic acid; and p represents 1 or 2, and pharmaceutically acceptable acid addition salts thereof.
Inventors
- 👤 Albert Sjoerdsma
- 👤 Philippe Bey
- 👤 Michel Jung
- 👤 Fritz Gerhart
- 👤 Daniel Schirlin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 07:32
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07C; C07C57/00; C07C57/52; C07C57/64; C07C57/76
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
160 words
A compound of the formula: ##STR50## wherein: R 1 is hydrogen, C 1 -C 6 alkyl or phenyl-(C 1 -C 4 alkyl); R 2 is hydrogen, C 1 -C 6 alkyl, phenyl-(C 1 -C 4 alkyl), or R 4 , where R 4 is as defined below; R 3 is hydrogen or, except when R 2 is R 4 , R 4 , where R 4 is as defined below; each R 4 , independently, is C 2 -C 5 alkylcarbonyl, phenylcarbonyl, phenyl-(C 1 -C 4 alkyl)carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of glycine or an L-aminocarboxylic acid of the formula HOCOCH(R 9 )NH 2 or HO--CO(CH 2 ) n CH(NH 2 )CO 2 H wherein R 9 is C 1 -C 4 alkyl, aminopropyl, aminobutyl, benzyl, or p-hydroxybenzyl and n is 1 or 2; and p is 1 or 2, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
160 words
A compound of the formula: ##STR50## wherein: R 1 is hydrogen, C 1 -C 6 alkyl or phenyl-(C 1 -C 4 alkyl); R 2 is hydrogen, C 1 -C 6 alkyl, phenyl-(C 1 -C 4 alkyl), or R 4 , where R 4 is as defined below; R 3 is hydrogen or, except when R 2 is R 4 , R 4 , where R 4 is as defined below; each R 4 , independently, is C 2 -C 5 alkylcarbonyl, phenylcarbonyl, phenyl-(C 1 -C 4 alkyl)carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of glycine or an L-aminocarboxylic acid of the formula HOCOCH(R 9 )NH 2 or HO--CO(CH 2 ) n CH(NH 2 )CO 2 H wherein R 9 is C 1 -C 4 alkyl, aminopropyl, aminobutyl, benzyl, or p-hydroxybenzyl and n is 1 or 2; and p is 1 or 2, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
16 words
A compound as defined in claim 1 wherein both R 1 and R 2 are hydrogen.
Claim 4
Dependent Claim
10 words
The compound as defined in claim 2 which is 1-fluoro-2,4-diaminobutane.
Claim 5
Dependent Claim
10 words
The compound as defined in claim 2 which is 1,1-difluoro-2,4-diaminobutane.
Claim 6
Dependent Claim
14 words
A compound as defined in claim 2 wherein R 3 is R 4 .
Claim 7
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 3 is hydrogen.
Claim 8
Dependent Claim
27 words
A compound as defined in claim 6 wherein R 1 is hydrogen and R 2 is (C 1 -C 4 alkyl) or phenyl-(C 1 -C 4 alkyl).
Claim 9
Dependent Claim
10 words
The compound as defined in claim 7 which is 1,1-difluoro-2-amino-4-benzylaminobutane.
Claim 10
Dependent Claim
19 words
A compound as defined in claim 6 wherein R 1 is hydrogen and R 2 is R 4 .
Claim 11
Dependent Claim
17 words
A compound as defined in claim 1, 2, 5, 6, 7, or 9 wherein p is 1.
Claim 12
Dependent Claim
17 words
A compound as defined in claim 1, 2, 5, 6, 7, or 9 wherein p is 2.
Claim 13
Dependent Claim
25 words
A pharmaceutical composition for inhibiting GABA-T comprising a GABA-T inhibiting effective amount of a compound as defined in claim 1 and a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
24 words
A pharmaceutical composition as defined in claim 12 wherein the compound is 1-fluoro-2,4-diaminobutane, 1,1-difluoro-2,4-diaminobutane, or 1,1-difluoro-2-amino-4-benzylaminobutane, or a pharmaceutically acceptable acid addition salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-06 | 1987-09-05 | 1988-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-06 | 1991-09-05 | 1992-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-06 | 1995-09-05 | 1996-03-06 | $7700.00 | Window Closed / Lapsed |