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WO1997032847A1 - Derives de pyrrolidone - Google Patents

Derives de pyrrolidone Download PDF

Info

Publication number
WO1997032847A1
WO1997032847A1 PCT/JP1997/000627 JP9700627W WO9732847A1 WO 1997032847 A1 WO1997032847 A1 WO 1997032847A1 JP 9700627 W JP9700627 W JP 9700627W WO 9732847 A1 WO9732847 A1 WO 9732847A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
protein phosphatase
formula
acid
protein
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.)
Ceased
Application number
PCT/JP1997/000627
Other languages
English (en)
Japanese (ja)
Inventor
Koshi Arai
Masakazu Sato
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.)
Taisho Pharmaceutical Co Ltd
Original Assignee
Taisho 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
Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Priority to AU18128/97A priority Critical patent/AU1812897A/en
Publication of WO1997032847A1 publication Critical patent/WO1997032847A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members

Definitions

  • the present invention relates to a pyridone derivative, and more particularly to a pyrrolidone derivative having a protein phosphatase inhibitory action.
  • Phosphorylation and dephosphorylation of proteins are one of the basic regulatory mechanisms of biological functions. Among them, many agents that inhibit protein kinases have been reported as antitumor agents. However, little has been reported on inhibitors of protein phosphatase, which also plays an essential role in cell growth. Protein dephosphorylation, like phosphorylation, plays a so-called “switch” role in protein activity, and it has recently been clearly shown that protein dephosphorylation controls the activity and inactivity of proteins in vivo. It is becoming.
  • the present invention provides a compound represented by the formula (I):
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • R 2 represents a cyano group or an acetyl group
  • an alkyl group having 1 to 20 carbon atoms is a linear or branched alkyl group having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, and a propyl group. And isopropyl, butyl, hexyl, hexadecyl, and octadecyl.
  • the compound of the present invention represented by the formula (I) can be synthesized by the following method. That is, according to the method described in Journal of the American's Chemical Society [J. Am. Chem. Soc. Vol. 81, p. 4355 (1959)], 2,3-dioxobutane And expression
  • the compound can be synthesized by treating a compound obtained by condensing the compound represented by the formula with an acid.
  • the acid used at this time include mineral acids such as hydrochloric acid, hydrobromic acid, nitric acid, and sulfuric acid, and sulfonic acids such as 10-camphorsulfonic acid, p-toluenesulfonic acid, and methanesulfonic acid. it can.
  • the acid treatment may be performed in a solvent, and a solvent such as dioxane, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, methylene chloride, chloroform, acetone, toluene, benzene and the like can be used as the solvent.
  • a solvent such as dioxane, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, methylene chloride, chloroform, acetone, toluene, benzene and the like can be used as the solvent.
  • tablets, pills, capsules, granules, solutions, emulsions, and suspensions can be prepared by using the compound as it is or by formulating it according to a conventional method. It can be prepared as an injection or the like and administered orally or parenterally.
  • Dosage should be administered to adult patients in the range of l to 1000 mg for oral administration and 0.01 to 10 Omg for parenteral administration once to several times a day. Can be. This dosage can be appropriately increased or decreased depending on the type of the disease, the age, weight, and symptoms of the patient.
  • the compound was prepared by dissolving in dimethyl sulfoxide.
  • Human cell-derived protein phosphatase was prepared using Escherichia coli transfected with VHR gene.
  • the protein tyrosine phosphatase CD45 was prepared from the cell membrane of the cultured cell Ba11-1.
  • the compound of the present invention inhibits protein phosphatase Since it has an action, it is useful as a therapeutic agent for diseases caused by protein phosphatase, such as an antitumor agent, an immunosuppressant, and a therapeutic agent for diabetes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Dérivés de pyrrolidone représentés par la formule générale (I), dans laquelle R1 représente hydrogène ou alkyle C¿1-20 et R?2 représente cyano ou acétyle. Ils sont efficaces en tant que remèdes contre les maladies induites par la protéine déphosphorylase, à titre d'agent antitumoral, agent immunodépresseurs et médicament contre le diabète.
PCT/JP1997/000627 1996-03-04 1997-03-03 Derives de pyrrolidone Ceased WO1997032847A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18128/97A AU1812897A (en) 1996-03-04 1997-03-03 Pyrrolidone derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4526296 1996-03-04
JP8/45262 1996-03-04

Publications (1)

Publication Number Publication Date
WO1997032847A1 true WO1997032847A1 (fr) 1997-09-12

Family

ID=12714386

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/000627 Ceased WO1997032847A1 (fr) 1996-03-04 1997-03-03 Derives de pyrrolidone

Country Status (2)

Country Link
AU (1) AU1812897A (fr)
WO (1) WO1997032847A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2583678A2 (fr) 2004-06-24 2013-04-24 Novartis Vaccines and Diagnostics, Inc. Immunopotentiateurs de petites molécules et dosages pour leur détection

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0317057A (ja) * 1989-06-15 1991-01-25 Fujisawa Pharmaceut Co Ltd 新規５員環複素環化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0317057A (ja) * 1989-06-15 1991-01-25 Fujisawa Pharmaceut Co Ltd 新規５員環複素環化合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEM. BER., Vol. 108, No. 10, (1975), ROEBER, HUBERT et al., "Kondensation von 1,2-Diketonen mit 2-Cyanacetamid", p. 3262-3270. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2583678A2 (fr) 2004-06-24 2013-04-24 Novartis Vaccines and Diagnostics, Inc. Immunopotentiateurs de petites molécules et dosages pour leur détection

Also Published As

Publication number Publication date
AU1812897A (en) 1997-09-22

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