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US3975367A
Expired / Lapsed
US
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Arabinofuranosyl N4 -aminoacyl cytosine containing compounds
Assignee: Pharmacia and Upjohn Co
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Filing: 1974-08-30
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Granted: 1976-08-17
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Expires: 1994-08-30
Abstract
Abstract Certain new 1-(3',5'-O-Variable-β-D-arabinofuranosyl)-N 4 -α-aminoacylcytosines, for example, 1-(5'-O-palmitoyl-β-D-arabinofuranosyl)-N 4 -[N.sup.α-[N-(tert-butoxycarbonyl)glycyl]-L-arginyl]cytosine hydrochloride, have been found active against neoplastic cells, viruses, and as immunosuppressants. The 3'-O-, or 5'-O-, variability includes the hydrogen atom and acyl groups. The N 4 -α-aminoacyl group comprises α-amino acids, N-protected α-amino acids, and similar peptidyl sequences of α-amino acids. Acid addition salts are an embodiment of the invention.
Inventors
- 👤 Duane T. Gish
- 👤 Gary D. Gray
- 👤 William J. Wechter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 13:30
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
73 words
The compounds 1-(3'-O-Variable- and 5'-O-Variable-β-D-arabinofuranosyl)-N 4 -(α-aminoacyl)cytosines of the formula: ##SPC4## wherein R 1 and R 2 are hydrogen, or an acyl group comprising up to 21 carbon atoms, inclusive; Y is hydrogen, halogen, or alkyl-, hydroxyalkyl-, or haloalkyl of from 1 to 4 carbon atoms, inclusive; and R 3 is an α-aminoacyl group consisting of a single α-amino acid or up to 10 α-aminoacids linked as peptides, including acid addition salts thereof.
Claim 2
Dependent Claim
73 words
The compounds 1-(3'-O-Variable- and 5'-O-Variable-β-D-arabinofuranosyl)-N 4 -(α-aminoacyl)cytosines of the formula: ##SPC4## wherein R 1 and R 2 are hydrogen, or an acyl group comprising up to 21 carbon atoms, inclusive; Y is hydrogen, halogen, or alkyl-, hydroxyalkyl-, or haloalkyl of from 1 to 4 carbon atoms, inclusive; and R 3 is an α-aminoacyl group consisting of a single α-amino acid or up to 10 α-aminoacids linked as peptides, including acid addition salts thereof.
Claim 3
Dependent Claim
11 words
The compounds according to claim 1 wherein R 2 is hydrogen.
Claim 4
Dependent Claim
10 words
The compounds according to claim 2 wherein Y is hydrogen.
Claim 5
Dependent Claim
12 words
The compounds according to claim 3 wherein R 1 is carboxylic acyl.
Claim 6
Dependent Claim
22 words
The compounds according to claim 4 wherein the α-aminoacyl group comprises -L-arginine, phenylalanine, or lysine attached to the 4-nitrogen of the cytosine.
Claim 7
Dependent Claim
18 words
The compounds according to claim 5 wherein the α-aminoacyl group comprises glycine and arginine or glycine and phenylalanine.
Claim 8
Dependent Claim
12 words
The compounds according to claim 6 wherein the α-aminoacyl group is N.sup.α-[N-(tert-butoxycarbonyl)glycyl]-L-arginyl.
Claim 9
Dependent Claim
18 words
The compounds according to claim 7 wherein the 5'-O-carboxylic acyl group is palmitoyl, benzoyl, adamantoyl, or cyclohexane carbonyl.
Claim 10
Dependent Claim
10 words
The compound according to claim 8, 1-(5'-O-palmitoyl-β-D-arabinofuranosyl)-N 4 -[N.sup.α-[N-(tert-butoxycarbonyl)glycyl]-L-arginyl]cytosine hydrochloride.
Claim 11
Dependent Claim
9 words
The compound according to claim 8, 1-(5'-O-palmitoyl-β-D-arabenofuranosyl)-N 4 -[N-[N-[N-(tert-butoxycarbonyl)-glycyl]glycyl]-L-phenylalanyl]cytosine.
Claim 12
Dependent Claim
10 words
The compound according to claim 8, 1-(5'-O-benzoyl-β-D-arabinofuranosyl)-N 4 -[N.sup.α-[N-(tert-butoxycarbonyl)glycyl]L-arginyl]cytosine hydrochloride.
Claim 13
Dependent Claim
10 words
The compound according to claim 8, 1-(5'-O-adamantoyl-β-D-arabinofuranosyl)-N 4 -[N.sup.α-[N-(tert-butoxycarbonyl)glycyl]L-arginyl]cytosine hydrochloride.
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) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |