Patent EP0444829A2 successfully refreshed from Google Patents.
EP0444829A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Immunosuppressive compounds
Assignee: Fisons Ltd
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Filing: 1991-02-22
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Granted: —
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Expires: 2011-02-22
Abstract
Abstract Compounds of formula I, wherein R¹ represents H, OH, protected OH or alkoxy; R² represents H; R³ represents O or (H,OH); R⁴ represents methyl, ethyl, propyl or allyl; R⁵ represents OH, protected OH or alkoxy; R⁶ represents OH; R⁷ represents OH, alkoxy or NR⁸R⁹ where R⁸ and R⁹ independently represent H, alkyl or aryl; in addition, R¹ and R² may together represent a second bond between the carbon atoms to which they are attached; and R⁶ and R⁷ may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.
Inventors
- 👤 Martin Edward Cooper
- 👤 David Keith Donald
- 👤 Hirokazu Tanaka
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 17:45
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/16; C07D309/28; C07D309/30; A; A61; A61P; A61P37/00; A61P37/02; A61P37/06; C07C; C07C235/00; C07C235/02; C07C235/30; C07C403/00; C07C403/20; C07C69/00; C07C69/66; C07C69/73; C07C69/734; C07C69/738; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
117 words
A compound of formula I, wherein R¹ represents H, OH, protected OH or alkoxy; R2 represents H; R³ represents 0 or (H,OH); R⁴ represents methyl, ethyl, propyl or allyl; 5 R⁵ represents OH, protected OH or alkoxy; R⁶ represents OH; R⁷ represents OH, alkoxy or NR⁸R⁹ where R⁸ and R⁹ independently represent H, alkyl or aryl; in addition, R¹ and R² may together represent a second bond between the carbon atoms to which they are attached; and R⁶ and R⁷ may together represent 0; provided that when R¹ and R⁵ each represent OH, R² represents H, R³ represents (H,OH) and R⁴ represents allyl, then R⁶ and R⁷ do not together represent O; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
16 words
A compound of formula I, as claimed in claim 1, wherein R⁴ represents allyl or propyl.
Claim 3
Dependent Claim
17 words
A compound of formula I, as claimed in claim 1 or claim 2, wherein R⁷ represents alkoxy.
Claim 4
Dependent Claim
54 words
A compound of formula I, as claimed in claim 1, which is: Methyl 12-allyl-4,6-dimethoxy-19-[4-hydroxy-3-methoxy cyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-5,15,17-trihydroxy-nonadeca-10,18-dienoate, Methyl 12-allyl-4,6-dimethoxy-19-[4-hydroxy-3-methoxy cyclohexyl]-2,8,10,16,18-pentamethyl-5,13,15,17-tetrahydroxy -nonadeca-10,18-dienoate, Methyl 12-allyl-5,17-dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-nonadeca-10,14,18-trienoate, Methyl 12-allyl-5,17-dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoate, Methyl 5,17-dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxy cyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-12-propyl-nonadeca-10,14,18-trienoate, Methyl 5,17-dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxy cyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-12-propyl-nonadeca-10,18-dienoate, Methyl 12-allyl-5,17-dihydroxy-19-[3,4-dimethoxycyclohexyl] -13-oxo-2,8,10,16,18-pentamethyl-4,6,15-trimethoxy-nonadeca-10,18-dienoate, 5,17-Dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxycyclo hexyl]-13-oxo-2,8,10,16,18-pentamethyl-12-propyl-nonadeca-10,14,18-trienoic acid 1,5-lactone, 12-Allyl-4,6-dimethoxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-5,15,17-trihydroxy-nonadeca-10,18-dienoic acid 1,5-lactone, 5,17-Dihydroxy-4,6-dimethoxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-12-propyl -nonadeca-10,18-dienoic acid 1,5-lactone, 12-Allyl-5,17-dihydroxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-4,6-dimethyoxynonadeca-10,18 -dienoic acid, 12-Allyl-5,17-dihydroxy-19-[4-hydroxy-3-methoxycyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-4,6-dimethyoxynonadeca-10,18 -dienoic acid 1,5-lactone, or N-Methyl-12-allyl-5,17-dihydroxy-19-[4-hydroxy-3-methoxy cyclohexyl]-13-oxo-2,8,10,16,18-pentamethyl-4,6-dimethoxy nonadeca-10,18-dieneamide.
Claim 5
Dependent Claim
18 words
A compound of formula I, as defined in claim 1, but without proviso, for use as a medicament.
Claim 6
Dependent Claim
23 words
The use of a compound of formula I, as defined in claim 1, but without proviso, in the manufacture of an immunosuppressive agent.
Claim 7
Dependent Claim
25 words
A pharmaceutical composition comprising a compound of formula I, as defined in claim 1, but without proviso, and a pharmaceutically acceptable adjuvant, diluent or carrier.
Claim 8
Dependent Claim
409 words
A process for the production of a compound of formula I, as defined in claim 1 but without proviso, which comprises: (a) producing a compound of formula I in which R⁶ and R⁷ together represent O, by reduction of a compound of formula II, in which R¹ to R⁵ are as defined above and R¹⁰ represents O, in the presence of an amine or an acid addition salt thereof; (b) producing a compound of formula I in which R⁶ represents OH and R⁷ represents alkoxy, by reduction of a compound of formula II as defined in (a) above, in the presence of an amine or an acid addition salt thereof, and an alcohol of formula R⁷H; (c) producing a compound of formula I in which R⁶ and R⁷ each represent OH, by the action of an inorganic base on a compound of formula II as defined in (a) above except that R¹⁰ represents (H,OH); (d) producing a compound of formula I in which R⁶ and R⁷ together represent O, by reaction of a corresponding compound of formula I in which R⁶ and R⁷ each represent OH with an esterification reagent; (e) producing a compound of formula I in which R⁷ represents NR⁸R⁹ by reaction of a corresponding compound of formula I in which R⁶ and R⁷ together represent O with an amine of formula NHR⁸R⁹; (f) producing a compound of formula I in which R¹ and R² each represent H by selective reduction of a corresponding compound of formula I in which R¹ and R² together represent a second bond between the carbon atoms to which they are attached; (g) producing a compound of formula I in which R¹ and R² together represent a second bond between the carbon atoms to which they are attached, by elimination of H₂O from a corresponding compound of formula I in which R¹ represents OH and R² represent H; (h) producing a compound of formula I in which one or both of R¹ and R⁵ represent alkoxy by reacting a corresponding compound of formula I in which one or both of R¹ and R⁵ represent OH with an alkylating agent; (i) producing a compound of formula I in which R⁴ represents propyl, by reduction of a corresponding compound of formula I in which R⁴ represents allyl; or (j) producing a compound of formula I in which R³ represents (H,OH) by reduction of a corresponding compound of formula I in which R³ represents O.
References Cited (Backward Citations)
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