GB1368896A - Mycophenolic acid derivatives and process for production thereof - Google Patents

Mycophenolic acid derivatives and process for production thereof

Info

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
Application number
GB3553872A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chugai Pharmaceutical Co Ltd
Original Assignee
Chugai Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP5714171A external-priority patent/JPS5542993B1/ja
Priority claimed from JP5714271A external-priority patent/JPS5542994B1/ja
Priority claimed from JP1844772A external-priority patent/JPS5542995B2/ja
Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd
Publication of GB1368896A publication Critical patent/GB1368896A/en
Expired legal-status Critical Current

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.
GB3553872A 1971-07-31 1972-07-28 Mycophenolic acid derivatives and process for production thereof Expired GB1368896A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP5714171A JPS5542993B1 (en) 1971-07-31 1971-07-31
JP5714271A JPS5542994B1 (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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
DE2237549C3 (en) 1980-10-30
DE2237549B2 (en) 1980-03-06
FR2148113A1 (en) 1973-03-11
FR2148113B1 (en) 1976-04-16
DE2237549A1 (en) 1973-02-08

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee