GB1368896A - Mycophenolic acid derivatives and process for production thereof - Google Patents
Mycophenolic acid derivatives and process for production thereofInfo
- Publication number
- GB1368896A GB1368896A GB3553872A GB3553872A GB1368896A GB 1368896 A GB1368896 A GB 1368896A GB 3553872 A GB3553872 A GB 3553872A GB 3553872 A GB3553872 A GB 3553872A GB 1368896 A GB1368896 A GB 1368896A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- mycophenolic acid
- acid
- amine
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1368896 Mycophenolic acid derivatives CHUGAI SEIYAKU KK 28 July 1972 [31 July 1971 (2) 24 Feb 1972] 35538/72 Heading C2A Novel mycophenolic acid derivatives having the Formula (I) wherein R is a C 1-6 alkyl group or a C 1-6 alkenyl group, and R<SP>1</SP> is (a) -NH 2 , in which X is hydrogen, halogen, hydroxy, carboxy, sulphamoyl, nitro, cyano, phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 5 acyl, C 2 - C 5 alkoxycarbonyl, C 2 -C 5 acylamino, C 5 -C 7 dialkylaminoethoxycarbonyl, or C 2 -C 8 dialkylamino; X<SP>1</SP> and Y<SP>1</SP> are the same or different and each is hydroxy, nitro, carboxy or C 1 -C 4 alkyl; and X<SP>2</SP> is hydrogen, halogen or C 2 -C 8 dialkylamino, are prepared by either (i) reacting an R- esterified mycophenolic acid haloformate of Formula (II) in which R is as defined above and X<SP>3</SP> is halogen, with an amine of formula HR<SP>1</SP>; or (ii) when R<SP>1</SP> is -NH 2 , by reacting a mycophenolic acid ester of Formula (IV) in which R is as defined above, with a metal salt of cyanic acid. The reactions may be carried out in an inert solvent or in an excess of one of the reactants. Reaction (i) is preferably conducted in the presence of an acid binding agent, e.g. a tertiary organic amine which may be an excess of the amine of formula HR<SP>1</SP> or sodium or potassium bicarbonate. Reaction (ii) is preferably carried out in the presence of a strong acid (e.g. HCl, H 2 SO 4 or a trihalogenoacetic acid) using sodium or potassium cyanate. Any reactive or labile substituents in the amine HR<SP>1</SP> may be suitably protected before the preparative reaction. Compounds of Formula (II) above are prepared by subjecting mycophenolic acid to a conventional esterification procedure and then reacting the ester with phosgene. Pharmaceutical compositions having anticancer and anti-tumour activity comprise a mycophenolic acid derivative of Formula (I) hereinbefore, together with a pharmaceutically acceptable carrier or diluent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5714271A JPS5542994B1 (en) | 1971-07-31 | 1971-07-31 | |
| JP5714171A JPS5542993B1 (en) | 1971-07-31 | 1971-07-31 | |
| JP1844772A JPS5542995B2 (en) | 1972-02-24 | 1972-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1368896A true GB1368896A (en) | 1974-10-02 |
Family
ID=27282210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3553872A Expired GB1368896A (en) | 1971-07-31 | 1972-07-28 | Mycophenolic acid derivatives and process for production thereof |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2237549C3 (en) |
| FR (1) | FR2148113B1 (en) |
| GB (1) | GB1368896A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4686234A (en) * | 1985-11-27 | 1987-08-11 | Syntex (U.S.A) Inc. | Mycophenolic acid derivatives in the treatment of inflammatory diseases, in particular rheumatoid arthritis |
| US4725622A (en) * | 1986-01-23 | 1988-02-16 | Syntex (U.S.A.) Inc. | Mycophenolic acid derivatives in the treatment of rheumatoid arthritis |
-
1972
- 1972-07-28 GB GB3553872A patent/GB1368896A/en not_active Expired
- 1972-07-31 DE DE19722237549 patent/DE2237549C3/en not_active Expired
- 1972-07-31 FR FR7227513A patent/FR2148113B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2237549A1 (en) | 1973-02-08 |
| DE2237549C3 (en) | 1980-10-30 |
| DE2237549B2 (en) | 1980-03-06 |
| FR2148113A1 (en) | 1973-03-11 |
| FR2148113B1 (en) | 1976-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |