US4565863A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Retinoid carbohydrates
Assignee: F Hoffmann La Roche AG
•
Filing: 1984-12-03
•
Granted: 1986-01-21
•
Expires: 2004-12-03
Abstract
Abstract The novel retinoids of the formula <IMAGE> I wherein R represents a residue of a sugar attached ester-wise or a residue of an amino-sugar attached amide-wise or of derivatives of such sugars and n is 1 or 2, can be used as medicaments, e.g. for the treatment of neoplasms, acne and psoriasis. These compounds are obtained by reacting a sugar or an aminosugar or a derivative thereof with a reactive derivative of 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid, optionally followed by the modification of reactive groups present in the reaction product.
Inventors
- 👤 Werner Bollag
- 👤 Hans J. Mayer
- 👤 Pierre-Charles Wyss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 22:43
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; A; A61; A61P; A61P17/00; A61P3/00; A61P3/02; A61P35/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
129 words
A retinoid of the formula: ##STR3## wherein n is 1 or 2; R is XR 1 ; X is --O--, --NH-- or --NH(CH 2 ) m --O--; m is an integer of from 2 to 6; and R 1 is a residue obtained by removal of a hydroxy group from a member selected from the group consisting of a sugar, an aminosugar, a deoxyaminosugar, deoxysugar, loweralkyl glycosides thereof, derivatives thereof wherein one or more of the hydroxy or amino groups contained therein are acylated with a lower alkanoyl, derivatives thereof wherein at least two of the hydroxy groups contained therein are acetalized and derivatives thereof where the free --CH 2 OH group is oxidized to a --COOH group; with said sugars being mono- or di-saccharides of pentoses or hexoses.
Claim 2
Dependent Claim
129 words
A retinoid of the formula: ##STR3## wherein n is 1 or 2; R is XR 1 ; X is --O--, --NH-- or --NH(CH 2 ) m --O--; m is an integer of from 2 to 6; and R 1 is a residue obtained by removal of a hydroxy group from a member selected from the group consisting of a sugar, an aminosugar, a deoxyaminosugar, deoxysugar, loweralkyl glycosides thereof, derivatives thereof wherein one or more of the hydroxy or amino groups contained therein are acylated with a lower alkanoyl, derivatives thereof wherein at least two of the hydroxy groups contained therein are acetalized and derivatives thereof where the free --CH 2 OH group is oxidized to a --COOH group; with said sugars being mono- or di-saccharides of pentoses or hexoses.
Claim 3
Dependent Claim
11 words
The retinoid of claim 1 wherein R 1 is a sugar.
Claim 4
Dependent Claim
13 words
The retinoid of claim 2 wherein said sugar is a pentose or hexose.
Claim 5
Dependent Claim
10 words
The retinoid of claim 3 wherein said retinoid is D-glucopyranosyl-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate.
Claim 6
Dependent Claim
11 words
The retinoid of claim 3 wherein said retinoid is D-ribofuranosyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate.
Claim 7
Dependent Claim
11 words
The retinoid of claim 2 wherein said sugar is a disaccharide.
Claim 8
Dependent Claim
10 words
The retinoid of claim 6 wherein said retinoid is 6,6-bis-O-[9-(4-methoxy-2,3,6,-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-D-trehalose.
Claim 9
Dependent Claim
11 words
The retinoid of claim 6 wherein said retinoid is [4-O-α-D-Glucopyranosyl-D-glucopyranoxyl] 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate.
Claim 10
Dependent Claim
13 words
The retinoid of claim 1 wherein said retinoid is a lower alkyl glycoside.
Claim 11
Dependent Claim
11 words
The retinoid of claim 9 wherein said retinoid is [methyl] 2,6-bis-O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-α-D-glucopyranoside.
Claim 12
Dependent Claim
11 words
The retinoid of claim 9 wherein said retinoid is [methyl] 4O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-α-D-glucopyranoside.
Claim 13
Dependent Claim
11 words
The retinoid of claim 9 wherein said retinoid is [methyl] 2-O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-α-D-glucopyranoside.
Claim 14
Dependent Claim
11 words
The retinoid of claim 9 wherein said retinoid is [methyl] 6-O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-α-D-glucopyranoside.
Claim 15
Dependent Claim
12 words
The retinoid of claim 1 wherein R 1 is an amino sugar.
Claim 16
Dependent Claim
10 words
The retinoid of claim 14 wherein said retinoid is 2-deoxy-2-[9-(4-methoxy-2,3,6-dimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenamido]-D-glucose.
Claim 17
Dependent Claim
22 words
The retinoid of claim 1 wherein R 1 is an amino sugar wherein one or more hydroxy or amino groups are acylated.
Claim 18
Dependent Claim
10 words
The retinoid of claim 16 wherein said retinoid is [2-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenamido]ethyl]2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside.
Claim 19
Dependent Claim
11 words
The retinoid of claim 16 wherein said retinoid is [2-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenamido]ethyl] 2-acetamido-2-deoxy-β-D-glucopyranoside.
Claim 20
Dependent Claim
10 words
The retinoid of claim 16 wherein said retinoid is 2-acetamido-2-deoxy-1,6-bis-O-[9(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-D-glucose.
Claim 21
Dependent Claim
12 words
The retinoid of claim 1 wherein R 1 is a deoxy sugar.
Claim 22
Dependent Claim
10 words
The retinoid of claim 20 wherein said retinoid is 1-O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-L-rhamnose.
Claim 23
Dependent Claim
25 words
The retinoid of claim 1 wherein R 1 is a derivative of a sugar where at least two of the free hydroxy groups are acetalized.
Claim 24
Dependent Claim
10 words
The retinoid of claim 22 wherein said retinoid is 4,6,-ethylidene-1-O-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]-D-glucose.
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) | 1989-01-20 | 1989-07-22 | 1990-01-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-20 | 1993-07-22 | 1994-01-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-20 | 1997-07-22 | 1998-01-21 | $7700.00 | Window Closed / Lapsed |