US4216208A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-Acyl derivatives of glucosamines having antitumor chemotherapeutic activity
Assignee: Proter SpA
•
Filing: 1978-07-31
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Granted: 1980-08-05
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Expires: 1998-07-31
Abstract
Abstract N-Acyl derivatives of glucosamines made by linking an amino acid or oligopeptide having a m-di(2-chloroethyl)amino-L-phenylalanyl group, to the amino group of the glucosamines by a peptide bond, are endowed with strong anti-tumor action against transplanted neoplasma in animal. The compounds according to the present invention are of the general formula (I): <IMAGE> where R1 is a hydrogen atom or an acetyl group, R2 is a hydrogen atom, an acetyl group, aliphatic (C1-C6) group or a benzyl group and R3 is m-di(2-chloroethyl) amino-L-phenylalanine, or L- methionyl -m-di(2-chloroethyl) amino-L-phenylalanyl-p-fluoro-L-phenylalanine, or p-fluoro-L-phenylalanyl-m-di (2-chloroethyl) amino-L-phenylalanyl-L-proline, or m-di (2-chloroethyl) amino-L-phenylalanyl-L-methionyl-p-fluoro-L-phenylalanine. The antineoplasmic activity of the compounds of the present invention is not affected in the gastrointestinal tract and hence they can be effectively administered orally.
Inventors
- 👤 Augusto De Barbieri
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:10
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
55 words
A N-acyl derivative of glucosamine selected from the group consisting of a compound of the formula: ##STR10## wherein: R 1 is --H, --COCH 3 ; R 2 is --H, --COCH 3 , C 1 to C 6 alkyl, or a benzyl group; ##STR11## or a salt thereof with an organic or inorganic acid physiologically tolerated.
Claim 2
Dependent Claim
55 words
A N-acyl derivative of glucosamine selected from the group consisting of a compound of the formula: ##STR10## wherein: R 1 is --H, --COCH 3 ; R 2 is --H, --COCH 3 , C 1 to C 6 alkyl, or a benzyl group; ##STR11## or a salt thereof with an organic or inorganic acid physiologically tolerated.
Claim 3
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of 1,3,4,6-tetra-O-acetyl-D-glucosamyl-m-di(2-chloroethyl)amino-L-phenylalanine and its salts with organic or inorganic acids physiologically tolerated.
Claim 4
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of D-ethyl-glucosamyl-m-di-(2-chloroethyl)amino-L-phenylalanine and its salts with organic or inorganic acids physiologically tolerated.
Claim 5
Dependent Claim
26 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of 1,3,4,6-tetra-O-acetyl-D-glucosamyl-p-fluoro-L-phenylalanyl-m-di(2-chloroethyl) amino-L-phenylalanyl-L-proline and its salts with organic or inorganic acids physiologically tolerated.
Claim 6
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of D-ethyl-glucosamyl-p-fluoro-L-phenylalanyl-m-di(2-chloroethyl)amino-L-phenylalanyl-L-proline and its salts with organic or inorganic acids physiologically tolerated.
Claim 7
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of D-glucosamyl-p-fluoro-L-phenylalanyl-m-di(2-chloroethyl)amino-L-phenylanyl-L-proline and its salts with organic and inorganic acids physiologically tolerated.
Claim 8
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of D-ethyl-glucosamyl-m-di(2-chloroethyl)amino-L-phenylalanyl-L-methionyl-p-fluoro-L-phenylalanine and its salts with organic and inorganic acids physiologically tolerated.
Claim 9
Dependent Claim
25 words
A N-acyl derivative as claimed in claim 1 selected from the group consisting of 1,3,4,6-tetra-O-acetyl-D-glucosamyl-L-methionyl-m-di(2-chloroethyl)amino-L-phenylalanyl-p-fluoro-L-phenylalanine and its salts with organic or inorganic acids physiologically tolerated.
Claim 10
Dependent Claim
24 words
A N-acyl derivative according to claim 1 selected from the group consisting of D-glucosamyl-L-methionyl-m-di(chloroethyl)amino-L-phenylalanyl-p-fluoro-L-phenylalanine and its salts with organic and inorganic acids physiologically tolerated.
Claim 11
Dependent Claim
24 words
A N-acyl derivative according to claim 1 selected from the group consisting of D-methyl-glucosamyl-L-methionyl-m-di-(chloroethyl)amino-L-phenylalanyl-p-fluoro-L-phenylalanine and its salts with organic or inorganic acids physiologically tolerated.
Claim 12
Dependent Claim
24 words
A N-acyl derivative according to claim 1 selected from the group consisting of D-ethyl-glucosamyl-L-methionyl-m-di(2-chloroethyl)amino-L-phenylalanyl-p-fluoro-L-phenylalanine and its salts with organic or inorganic acids physiologically tolerated.
Claim 13
Dependent Claim
23 words
A N-acyl derivative according to claim 1 wherein R 2 is --H, --COCH 3 , C 1 to C 6 alkyl, or benzyl.
Claim 14
Dependent Claim
38 words
A pharmaceutical composition which is effective in controlling transplanted neoplasms in animals comprising at least one N-acyl derivative of glucosamine as defined in any one of claims 1 through 12 as an active ingredient in a pharmaceutical carrier.
Claim 15
Dependent Claim
46 words
A method for chemotherapeutic treatment of a transplanted neoplastic disease in animals comprising administering a composition comprising at least one N-acyl derivative of glucosamine as defined in claim 1 as an active ingredient in a physiologically tolerable amount which is effective to control said neoplastic disease.
Claim 16
Dependent Claim
14 words
The method according to claim 14 wherein said composition is administered orally or parenterally.
Claim 17
Dependent Claim
14 words
The method according to claim 14 wherein said composition is administered in successive doses.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-08-05 | 1984-02-04 | 1984-08-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-08-05 | 1988-02-04 | 1988-08-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-08-05 | 1992-02-04 | 1992-08-05 | $7700.00 | Window Closed / Lapsed |