US4316983A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Neoplasmic compounds: sugar esters and glycosides
Assignee: Hoffmann La Roche Inc
•
Filing: 1980-06-12
•
Granted: 1982-02-23
•
Expires: 2000-06-12
Abstract
Abstract The invention relates to novel sugar esters and glycosides especially derivatives of D-glucopyranoside and D-glucopyranaronate suitable for the treatment of neoplasms, acne, psoriasis and dermatoses.
Inventors
- 👤 Werner Bollag
- 👤 Pierre-Charles Wyss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:58
CPC Classifications
C; C07; C07H; C07H3/00; C07C; C07C33/00; C07C33/38; A; A61; A61P; A61P17/00; A61P29/00; A61P35/00; A61P37/00; A61P37/08; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C07C63/00; C07C63/33; C07C63/49; C07H13/00; C07H13/02; C07H13/08; C07H15/00; C07H15/02; C07H15/04; C07H15/18
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
232 words
Compounds of the general formula: ##STR11## where R 1 represents a group of the formula --CH 2 OH, --CH 2 OR 6 , --COR 7 or --CONH 2 ; R 2 represents hydrogen or lower alkanoyl; R 3 and R 4 represent hydrogen or lower alkanoyl or a group R 6 ; R 5 represents lower alkoxy or a group of the formula OR 6 or OR 8 ; R 6 represents a group of the formula: ##STR12## R 7 represents hydroxy, lower alkoxy or OM in which M represents a cation; and R 8 represents a group of the formula: ##STR13## providing that: (i) R 1 represents a group of the formula --CH 2 OR 6 , R 2 represents hydrogen and one of R 3 and R 4 hydrogen and the other represents a group R 6 when R 5 represents lower alkoxy; (ii) R 1 represents a group of the formula --COR 7 and R 2 , R 3 and R 4 represent lower alkanoyl when R 5 represents a group of the formula OR 6 ; or (iii) R 1 represents a group of the formula --CH 2 OH, --COR 7 or --CONH 2 and R 2 , R 3 and R 4 represent hydrogen of lower alkanoyl when R 5 represents a group of the formula OR 8 ; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
232 words
Compounds of the general formula: ##STR11## where R 1 represents a group of the formula --CH 2 OH, --CH 2 OR 6 , --COR 7 or --CONH 2 ; R 2 represents hydrogen or lower alkanoyl; R 3 and R 4 represent hydrogen or lower alkanoyl or a group R 6 ; R 5 represents lower alkoxy or a group of the formula OR 6 or OR 8 ; R 6 represents a group of the formula: ##STR12## R 7 represents hydroxy, lower alkoxy or OM in which M represents a cation; and R 8 represents a group of the formula: ##STR13## providing that: (i) R 1 represents a group of the formula --CH 2 OR 6 , R 2 represents hydrogen and one of R 3 and R 4 hydrogen and the other represents a group R 6 when R 5 represents lower alkoxy; (ii) R 1 represents a group of the formula --COR 7 and R 2 , R 3 and R 4 represent lower alkanoyl when R 5 represents a group of the formula OR 6 ; or (iii) R 1 represents a group of the formula --CH 2 OH, --COR 7 or --CONH 2 and R 2 , R 3 and R 4 represent hydrogen of lower alkanoyl when R 5 represents a group of the formula OR 8 ; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
40 words
Compounds according to claim 1 wherein the compound has formula: ##STR14## wherein R 51 represents lower alkoxy and one of R 31 and R 41 represents a group R 6 as defined in claim 1 and the other represents hydrogen.
Claim 4
Dependent Claim
35 words
Compounds in accordance with claim 1 of the general formula: ##STR15## wherein R 22 , R 32 and R 42 represent lower alkanoyl and R 6 and R 7 are as defined in claim 1.
Claim 5
Dependent Claim
53 words
Compounds according to claim 1 wherein the compound has the general formula: ##STR16## wherein R 11 represents a group of the formula --CH 2 OH, --COR 7 or --CONH 2 , R 23 , R 33 , R 43 represent hydrogen or lower alkanoyl and R 8 is as defined in claim 1.
Claim 6
Dependent Claim
10 words
Compounds according to claim 2, wherein R 51 represents methoxy.
Claim 7
Dependent Claim
10 words
Compounds according to claim 3, wherein R 7 represents methoxy.
Claim 8
Dependent Claim
18 words
Compounds according to claim 4, wherein R 11 represents a group of the formula --CONH 2 or --COONa.
Claim 9
Dependent Claim
2 words
Methyl 2,6-bis-0-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]benzoyl]-α-D-glucopyranoside.
Claim 10
Dependent Claim
2 words
Methyl 2,6-bis-0-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]benzoyl]-α-D-glucopyranoside.
Claim 11
Dependent Claim
16 words
Methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranuronate; methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-β-D-glucopyranuronate; methyl-3,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside; p-[(E)-2-(5,6,7,8,-tetrahydro-5,5,8,8,-tetramethyl-2-naphthyl)-propenyl]-benzyl-α-D-glucopyranoside; p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronamide; methyl [p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-2,3,4-tri-O-acetyl-β-D-glucopyranoside]-uronate; methyl [p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside]-uronate; sodium p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronate or p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronic acid.
Claim 12
Dependent Claim
16 words
Methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranuronate; methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-β-D-glucopyranuronate; methyl-3,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside; p-[(E)-2-(5,6,7,8,-tetrahydro-5,5,8,8,-tetramethyl-2-naphthyl)-propenyl]-benzyl-α-D-glucopyranoside; p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronamide; methyl [p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-2,3,4-tri-O-acetyl-β-D-glucopyranoside]-uronate; methyl [p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside]-uronate; sodium p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronate or p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzyl-β-D-glucopyranoside-uronic acid.
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) | 1985-02-22 | 1985-08-24 | 1986-02-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-22 | 1989-08-24 | 1990-02-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-22 | 1993-08-24 | 1994-02-23 | $7700.00 | Window Closed / Lapsed |