US5484809A
Expired / Lapsed
US
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Prodrugs for oral administration containing taxol or substituted taxol covalently bound to a phospholipid
Assignee: Nexstar Pharmaceuticals Inc
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Filing: 1994-12-14
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Granted: 1996-01-16
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Expires: 2014-12-14
Abstract
Abstract The oral delivery of many classes of drugs is facilitated by converting drugs having suitable functional groups to 1-O-alkyl-, 1-O-acyl-, 1-S-acyl, and 1-S-alkyl-sn-glycero-3-phosphate derivatives. The method confers the ability to be absorbed through the digestive tract to drugs that are not orally bioavailable in the non-derivatized state, and enhances the effectiveness of drugs that are poorly absorbed or rapidly eliminated. The method provides orally bioavailable lipid prodrugs of zaxol and taxol-related compounds. Potency of the lipid prodrugs is comparable to that of the corresponding nonderivatized drugs. In a preferred embodiment, taxol or substituted taxol is covalently bound to a phospholipid.
Inventors
- 👤 Karl Y. Hostetler
- 👤 Nagarajan C. Sridhar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:24
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/542; A61K47/543; A61K47/544; A61K47/548; A61K9/00; A61K9/10; A61K9/127; A61P; A61P35/00; B; B82; B82Y; B82Y5/00; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3886; C07F9/3891; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4062; C07F9/4065; C07F9/547; C07F9/655; C07F9/6551; C07F9/65512; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/16
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
81 words
An antineoplastic prodrug, comprising taxol, or a substituted taxol, covalently bound to a phospholipid compound, wherein said prodrug has the formula: ##STR4## wherein R 1 and R 2 are the same or different and are straight or branched, saturated or unsaturated C 8 -C 18 acyl or alkyl groups; or R 2 is benzyl or OH; R 3 is taxol, taxotene, baccatin III, or 10-deacetyl baccatin III; R 4 is benzoyl, pivaloyl, acetate, peptides, or amino acids; and n is 0-10.
Claim 2
Dependent Claim
81 words
An antineoplastic prodrug, comprising taxol, or a substituted taxol, covalently bound to a phospholipid compound, wherein said prodrug has the formula: ##STR4## wherein R 1 and R 2 are the same or different and are straight or branched, saturated or unsaturated C 8 -C 18 acyl or alkyl groups; or R 2 is benzyl or OH; R 3 is taxol, taxotene, baccatin III, or 10-deacetyl baccatin III; R 4 is benzoyl, pivaloyl, acetate, peptides, or amino acids; and n is 0-10.
Claim 3
Dependent Claim
26 words
The prodrug of claim 1, wherein said phospholipid is selected from the group consisting of phosphatidylglycerols, 1-O-alkyl-sn-glycero-3-phosphatidic acids, 1-O-acyl-sn-glycero-3-phosphatidic acids, 1 -S-alkyl-sn-glycero-3-phosphatidic acids, and 1-S-acyl-sn-glycero-3-phosphatidic acids.
Claim 4
Dependent Claim
24 words
The taxol prodrug of claim 1, wherein said substituted taxol is taxol having lipophilic substituents at the β-amino group of the taxol side chain.
Claim 5
Dependent Claim
23 words
The prodrug of claim 3, wherein said lipophilic substituents are selected from the group consisting of benzoyl, pivaloyl, acetate, peptides, and amino acids.
Claim 6
Dependent Claim
23 words
The prodrug of claim 1, wherein R 1 is an ether linked alkyl group; R 2 is OH, and R 4 is benzoyl.
Claim 7
Dependent Claim
10 words
The prodrug of claim 1: wherein R 1 is 1-O-octadecyl.
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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) | 1999-01-15 | 1999-07-17 | 2000-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-01-15 | 2003-07-17 | 2004-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-01-15 | 2007-07-17 | 2008-01-16 | $7700.00 | Window Closed / Lapsed |