Patent US2368643A successfully refreshed from Google Patents.
US4291024A
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Cytotoxic liponucleotide analogs
Assignee: University of Rhode Island
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Filing: 1980-01-18
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Granted: 1981-09-22
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Expires: 2000-01-18
Abstract
Abstract Nucleotides of nucleosides or bases having known cytotoxic activity are reacted to form corresponding cytotoxic liponucleotide analogs by phosphorylation of molecular species of phosphatidic acids. The resulting cytotoxic liponucleotide analogs exhibit an enhanced therapeutic index and broader spectrum of antitumor activity as compared to the parent nucleoside or base compounds, apparently due to an improved selective uptake thereof by metabolizing tumor cells, and are thus useful cytotoxic, antiviral and antineoplastic agents.
Inventors
- 👤 Joseph G. Turcotte
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 23:58
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
157 words
A compound selected from the group consisting of compounds of the formula: ##STR9## in which: R 1 and R 2 are each predominantly straight, saturated or unsaturated multispecies fatty chains of 6-24 carbon atoms each; at least one of A 1 , A 2 and A 3 is methylene and the others of A 1 , A 2 and A 3 are each independently divalent oxygen or methylene; B 1 and B 2 are each independently divalent oxygen (--O--), methylene (--CH 2 --), ester ##STR10## or amide ##STR11## functions; X is a nucleoside base selected from the group consisting of cytosine, uracil, thymine, adenine, guanine, dihydrouracil, 5-fluorouracil, 5-azauracil, 6-azauracil, 5-azacytosine, 6-azacytosine, tetrahydropyridine dione, 2-amino tetrahydropyridine dione, 6-mercaptopurine, thioguanine, selenoguanine, 8-azaadenine-7-carboxamide and N-methyl-2-amino-1,2,4-triazolopurine; sugar is selected from the group consisting of ribose, deoxyribose, lyxose, xylose and arabinose, provided that the sugar is not ribose or deoxyribose when the heterocycle is cytosine; and their physiologically acceptable acid addition salts.
Claim 2
Dependent Claim
157 words
A compound selected from the group consisting of compounds of the formula: ##STR9## in which: R 1 and R 2 are each predominantly straight, saturated or unsaturated multispecies fatty chains of 6-24 carbon atoms each; at least one of A 1 , A 2 and A 3 is methylene and the others of A 1 , A 2 and A 3 are each independently divalent oxygen or methylene; B 1 and B 2 are each independently divalent oxygen (--O--), methylene (--CH 2 --), ester ##STR10## or amide ##STR11## functions; X is a nucleoside base selected from the group consisting of cytosine, uracil, thymine, adenine, guanine, dihydrouracil, 5-fluorouracil, 5-azauracil, 6-azauracil, 5-azacytosine, 6-azacytosine, tetrahydropyridine dione, 2-amino tetrahydropyridine dione, 6-mercaptopurine, thioguanine, selenoguanine, 8-azaadenine-7-carboxamide and N-methyl-2-amino-1,2,4-triazolopurine; sugar is selected from the group consisting of ribose, deoxyribose, lyxose, xylose and arabinose, provided that the sugar is not ribose or deoxyribose when the heterocycle is cytosine; and their physiologically acceptable acid addition salts.
Claim 3
Dependent Claim
21 words
A compound according to claim 1, wherein at least one of A 1 , A 2 and A 3 is oxygen.
Claim 4
Dependent Claim
20 words
A compound according to claim 1, wherein A 1 is methylene while A 2 and A 3 are both oxygen.
Claim 5
Dependent Claim
20 words
A compound according to claim 1, wherein A 2 is methylene while A 1 and A 3 are both oxygen.
Claim 6
Dependent Claim
16 words
A compound according to claim 1, wherein B 1 and B 2 are each ester groups.
Claim 7
Dependent Claim
18 words
A compound according to claim 1, wherein R 1 is predominately saturated and R 2 is predominately unsaturated.
Claim 8
Dependent Claim
24 words
A pharmaceutical composition comprising a safe and cytotoxically effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
162 words
A compound selected from the group consisting of compounds of the formula: ##STR12## in which: R 1 and R 2 are each predominantly straight, saturated or unsaturated multispecies fatty chains of 6-24 carbon atoms each, provided that R 1 does not equal R 2 when R 1 is CH 3 (CH 2 ) 14 CO--; A 1 , A 2 and A 3 are each independently divalent oxygen or methylene; B 1 and B 2 are each independently divalent oxygen (--O--), methylene (--CH 2 --), ester ##STR13## or amide ##STR14## functions; X is a nucleoside base selected from the group consisting of cytosine, uracil, thymine, adenine, guanine, dihydrouracil, 5-fluorouracil, 5-azauracil, 6-azauracil, 5-azacytosine, 6-azacytosine, tetrahydropyridine dione, 2-aminotetrahydropyridine dione, 6-mercaptopurine, thioguanine, selenoguanine, 8-azaadenine-7-carboxamide and N-methyl-2-amino-1,2,4-triazolopurine; sugar is selected from the group consisting of ribose, deoxyribose, lyxose, xylose and arabinose, provided that the sugar is not ribose or deoxyribose when the heterocycle is cytosine, uracil, adenine or guanine; and their physiologically acceptable acid addition salts.
Claim 10
Dependent Claim
162 words
A compound selected from the group consisting of compounds of the formula: ##STR12## in which: R 1 and R 2 are each predominantly straight, saturated or unsaturated multispecies fatty chains of 6-24 carbon atoms each, provided that R 1 does not equal R 2 when R 1 is CH 3 (CH 2 ) 14 CO--; A 1 , A 2 and A 3 are each independently divalent oxygen or methylene; B 1 and B 2 are each independently divalent oxygen (--O--), methylene (--CH 2 --), ester ##STR13## or amide ##STR14## functions; X is a nucleoside base selected from the group consisting of cytosine, uracil, thymine, adenine, guanine, dihydrouracil, 5-fluorouracil, 5-azauracil, 6-azauracil, 5-azacytosine, 6-azacytosine, tetrahydropyridine dione, 2-aminotetrahydropyridine dione, 6-mercaptopurine, thioguanine, selenoguanine, 8-azaadenine-7-carboxamide and N-methyl-2-amino-1,2,4-triazolopurine; sugar is selected from the group consisting of ribose, deoxyribose, lyxose, xylose and arabinose, provided that the sugar is not ribose or deoxyribose when the heterocycle is cytosine, uracil, adenine or guanine; and their physiologically acceptable acid addition salts.
Claim 11
Dependent Claim
21 words
A compound according to claim 8, wherein at least one of A 1 , A 2 and A 3 is oxygen.
Claim 12
Dependent Claim
20 words
A compound according to claim 8, wherein A 2 is methylene while A 1 and A 3 are both oxygen.
Claim 13
Dependent Claim
16 words
A compound according to claim 8, wherein B 1 and B 2 are each ester groups.
Claim 14
Dependent Claim
18 words
A compound according to claim 8, wherein R 1 is predominately saturated and R 2 is predominately unsaturated.
Claim 15
Dependent Claim
24 words
A pharmaceutical composition comprising a safe and cytotoxically effective amount of a compound according to claim 8 in combination with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
US3787392A
Cited
US3872083A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-21 | 1985-03-23 | 1985-09-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-21 | 1989-03-23 | 1989-09-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-21 | 1993-03-23 | 1993-09-22 | $7700.00 | Window Closed / Lapsed |