GB1077689A - Derivatives of 3-methylpurine and methods of preparing the same - Google Patents

Derivatives of 3-methylpurine and methods of preparing the same

Info

Publication number
GB1077689A
GB1077689A GB342466A GB342466A GB1077689A GB 1077689 A GB1077689 A GB 1077689A GB 342466 A GB342466 A GB 342466A GB 342466 A GB342466 A GB 342466A GB 1077689 A GB1077689 A GB 1077689A
Authority
GB
United Kingdom
Prior art keywords
methyl
prepared
pyridyl
methoxy
reacting
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
GB342466A
Inventor
Felix G Bergmann
Zohan Neiman
Mordechai Kleiner
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.)
Yissum Research Development Co of Hebrew University of Jerusalem
Original Assignee
Yissum Research Development Co of Hebrew University of Jerusalem
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 Yissum Research Development Co of Hebrew University of Jerusalem filed Critical Yissum Research Development Co of Hebrew University of Jerusalem
Publication of GB1077689A publication Critical patent/GB1077689A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/36—Sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/20—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/28—Oxygen atom
    • C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/36—Sulfur atom
    • C07D473/38—Sulfur atom attached in position 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6

Landscapes

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

Abstract

The invention comprises 3-methylpurine derivatives of the general formula <FORM:1077689/C2/1> wherein R represents hydrogen and X represents chlorine or methoxy or R represents an aromatic group or a heterocyclic group of aromatic character and X represents hydrogen, chlorine, methoxy, methylamino or dimethylamino. The 6-chloro-3-methylpyrines of the above general formula may be prepared by reacting the corresponding 3-methyl-6-methylthio purines with gaseous chlorine in metahnol solution at a temperature below - 3 DEG C. and the 6-chloro-atom of said purines may be replaced by methoxy, ethoxy, methylamino, dimethylamino or thiono groups by reaction with methanol, ethanol, methylamine, dimethylamine and ammonium sulphide respectively. 6-Methylamino or dimethylamino compounds of the invention may also be prepared by reacting the corresponding 3-methyl-6-methylthio purines with methylamine or dimethylamine. 3-Methyl-8-phenylpurine may be prepared by desulphuration of 3-methyl-6-methylthio-8-phenylpurine with Raney nickel and 3-methyl-8(31-pyridyl)purine by desulphuration of 2,6-dithio-3-methyl-8-(31-pyridyl)purine with Raney nickel. Other 3-methylpurines of the invention wherein R is aromatic or heterocyclic and X is hydrogen may be prepared in similar manner. 3-Methylhypoxanthines of the general Formula II may be prepared by heating the corresponding 6-chloro-3-methylpurine with sodium acetate in aqueous acetic acid or by reacting the corresponding 6-methoxy-3-mehtylpurine with aqueous hydrochloric acid. 3-Methyl-8-phenylhypoxanthine may also be prepared by condensing 4,5 - diamino - 6 - hydroxy - 3-methyl pyrimidine with benzamide hydrochloride in the presence of sodium acetate. 2,6 - Dithio - 3 - methyl - 8 - (31 - pyridyl)-purine may be prepared by heating 3-methyl-8-(31-pyridyl)-2-thioxanthine with phosphorus pentasulphide in pyridine. 3 - Methyl - 8 - (31 - pyridyl) - 2 - thioxanthine may be prepared by reacting 4,5-diamino-3-methyl-2-thiouracil with nicotinamidine hydrochloride and anhydrous sodium acetate.
GB342466A 1965-11-24 1966-01-26 Derivatives of 3-methylpurine and methods of preparing the same Expired GB1077689A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IL2467965A IL24679A (en) 1965-11-24 1965-11-24 Derivatives of 3-methyl purine and methods of preparing the same

Publications (1)

Publication Number Publication Date
GB1077689A true GB1077689A (en) 1967-08-02

Family

ID=11043766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB342466A Expired GB1077689A (en) 1965-11-24 1966-01-26 Derivatives of 3-methylpurine and methods of preparing the same

Country Status (2)

Country Link
GB (1) GB1077689A (en)
IL (1) IL24679A (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995000516A1 (en) * 1993-06-22 1995-01-05 Euro-Celtique S.A. Novel chemical compounds having pde-iv inhibition activity
US5591776A (en) * 1994-06-24 1997-01-07 Euro-Celtique, S.A. Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5744473A (en) * 1996-09-16 1998-04-28 Euro-Celtique, S.A. PDE IV inhibitors: "bis-compounds"
US5864037A (en) 1996-06-06 1999-01-26 Euro-Celtique, S.A. Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
WO1999031102A1 (en) * 1997-12-12 1999-06-24 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase iv inhibition activity
US5922751A (en) 1994-06-24 1999-07-13 Euro-Celtique, S.A. Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US5977119A (en) 1994-12-13 1999-11-02 Euro-Celtique, S.A. Trisubstituted thioxanthines
US6025361A (en) 1994-12-13 2000-02-15 Euro-Celtique, S.A. Trisubstituted thioxanthines
US6066641A (en) 1994-12-13 2000-05-23 Euro-Celtique S.A. Aryl thioxanthines
US6075016A (en) 1996-04-10 2000-06-13 Euro-Celtique S.A. 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US6166041A (en) 1995-10-11 2000-12-26 Euro-Celtique, S.A. 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6268373B1 (en) 1995-06-07 2001-07-31 Euro-Celtique S.A. Trisubstituted thioxanthines
US6294541B1 (en) 1996-06-06 2001-09-25 Euro-Celtique S.A. Purine derivatives having phosphodiesterase IV inhibition activity
US6319928B1 (en) 1998-11-30 2001-11-20 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase IV inhibition activity
US6413975B1 (en) 1999-04-02 2002-07-02 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase iv inhibition activity

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5939422A (en) 1993-06-22 1999-08-17 Euro-Celtique, S.A. Chemical compounds having PDE-IV inhibition activity
AU683270B2 (en) * 1993-06-22 1997-11-06 Euro-Celtique S.A. Novel chemical compounds having PDE-IV inhibition activity
WO1995000516A1 (en) * 1993-06-22 1995-01-05 Euro-Celtique S.A. Novel chemical compounds having pde-iv inhibition activity
EP0916673A1 (en) * 1993-06-22 1999-05-19 Euroceltique S.A. 6-Amino purine derivatives having PDE-IV inhibition activity
EP0916672A1 (en) * 1993-06-22 1999-05-19 Euroceltique S.A. 6-Amino purine derivatives having PDE-IV inhibition activity and intermediates
US5591776A (en) * 1994-06-24 1997-01-07 Euro-Celtique, S.A. Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5922751A (en) 1994-06-24 1999-07-13 Euro-Celtique, S.A. Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US5889014A (en) 1994-10-12 1999-03-30 Euro-Celtique, S.A. Heterocyclic compounds for inhibiting phosphodiesterase IV
US6066641A (en) 1994-12-13 2000-05-23 Euro-Celtique S.A. Aryl thioxanthines
US6025361A (en) 1994-12-13 2000-02-15 Euro-Celtique, S.A. Trisubstituted thioxanthines
US5977119A (en) 1994-12-13 1999-11-02 Euro-Celtique, S.A. Trisubstituted thioxanthines
US6153630A (en) 1995-01-10 2000-11-28 Euro-Celtique, S.A. Phenylpyridyl compounds for inhibiting phosphodiesterase IV and methods of using same
US6268373B1 (en) 1995-06-07 2001-07-31 Euro-Celtique S.A. Trisubstituted thioxanthines
US6166041A (en) 1995-10-11 2000-12-26 Euro-Celtique, S.A. 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6075016A (en) 1996-04-10 2000-06-13 Euro-Celtique S.A. 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
EP0912575A1 (en) * 1996-06-06 1999-05-06 Euro-Celtique S.A. Improved methods for the synthesis of chemical compounds having pde-iv inhibitory activity
US5864037A (en) 1996-06-06 1999-01-26 Euro-Celtique, S.A. Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
EP0912575A4 (en) * 1996-06-06 2001-04-25 Euro Celtique Sa Improved methods for the synthesis of chemical compounds having pde-iv inhibitory activity
US6294541B1 (en) 1996-06-06 2001-09-25 Euro-Celtique S.A. Purine derivatives having phosphodiesterase IV inhibition activity
US6310205B1 (en) 1996-06-06 2001-10-30 Euro-Celtique, S.A. Hypoxathine compounds
US5744473A (en) * 1996-09-16 1998-04-28 Euro-Celtique, S.A. PDE IV inhibitors: "bis-compounds"
WO1999031102A1 (en) * 1997-12-12 1999-06-24 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase iv inhibition activity
US6228859B1 (en) 1997-12-12 2001-05-08 Euro-Celtique S.A. Purine derivatives having phosphodiesterase IV inhibition activity
US6319928B1 (en) 1998-11-30 2001-11-20 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase IV inhibition activity
US6413975B1 (en) 1999-04-02 2002-07-02 Euro-Celtique, S.A. Purine derivatives having phosphodiesterase iv inhibition activity

Also Published As

Publication number Publication date
IL24679A (en) 1971-10-20

Similar Documents

Publication Publication Date Title
GB1077689A (en) Derivatives of 3-methylpurine and methods of preparing the same
US2957875A (en) Derivatives of purine
YAMAZAKI et al. Synthesis of thio-AICA, 6-thioxanthine, isoguanine analogs, and their ribosides
Robins Potential Purine Antagonists. IX. Further Studies of Some 4, 6-Disubstituted Pyrazolo [3, 4-d] pyrimidines1
GB1073137A (en) Purine n-oxide derivatives
GB939287A (en) New morphinone and codeinone derivatives and process for preparing the same
GB951431A (en) Pyrimidine derivatives and the manufacture thereof
Elion et al. Studies on Condensed Pyrimidine Systems. XI. Some 8-Alkyl-7-pteridones1
GB774095A (en) Improvements in or relating to pyrimidine compounds
GB744865A (en) Improvements relating to the preparation of 6-disubstituted-amino-purines
GB798646A (en) Improvements in and relating to derivatives of pyrimidine and the manufacture thereof
Russell et al. A New Condensed Pyrimidine System: Some p-Oxazino [2, 3-d] pyrimidines
GB1062386A (en) Process for preparing pyrazinyl phosphorothioates
GB810846A (en) New pyrimidine compounds and processes for producing the same
GB761944A (en) Novel xanthine derivatives and a process for the manufacture thereof
Hung THE REACTIONS OF DIAZONIUM IONS WITH PURINES AND PYRIMIDINES.
GB759981A (en) Process for the manufacture of xanthine derivatives
GB767588A (en) Substituted pyrimidine compounds
GB912788A (en) Phenylpiperazinylacyl anilines
GB710070A (en) New pyrimidine compounds and processes for their preparation
GB713259A (en) Improvements in or relating to processes for making derivatives of purine
GB1009439A (en) Purine derivatives and processes for their synthesis
GB744866A (en) Improvements relating to 2-substituted-mercapto-6-disubstituted-aminopurines and salts thereof
Ukponmwan et al. Physical characteristics of synthesized 1, 4-bis (arylamino)-2-(aryloxy) anthraquinone dyes for synthetic polymer fibers
GB718689A (en) A new pyrimidine compound and the manufacture thereof