GB744867A - Improvements relating to 2-substituted-mercapto-4-amino-6-disubstituted-aminopyrimidines and acid addition salts thereof - Google Patents

Improvements relating to 2-substituted-mercapto-4-amino-6-disubstituted-aminopyrimidines and acid addition salts thereof

Info

Publication number
GB744867A
GB744867A GB26313/53A GB2631353A GB744867A GB 744867 A GB744867 A GB 744867A GB 26313/53 A GB26313/53 A GB 26313/53A GB 2631353 A GB2631353 A GB 2631353A GB 744867 A GB744867 A GB 744867A
Authority
GB
United Kingdom
Prior art keywords
amino
methylthio
substituted
mercapto
mononuclear
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
GB26313/53A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB744867A publication Critical patent/GB744867A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom

Landscapes

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

Abstract

The invention comprises pyrimidine derivatives of the formula <FORM:0744867/IV(a)/1> where R1 is alkyl or mononuclear aralkyl and R2 and R3 are alkyl, mononuclear aryl or mononuclear aralkyl or with the N atom form a 6-membered ring. These are made by heating the corresponding 6-halogen compounds with HNR2R3 to 80-140 DEG C. (preferably 100-130 DEG C.), if desired in an inert solvent. The products form salts with strong acids such as hydrochloric, sulphuric and picric. They can be used for making purine derivatives as in Specifications 744,866 and 744,869. Examples show the production of the following substituted pyrimidines: 2-methylthio-4-amino-6-dimethylamino, 2 - methylthio - 4 - amino - 6-diethylamino, 2 - methylthio - 4 - amino - 6-butylbenzylamino, 2 - methylthio - 4 - amino-6 - N - methylanilino, 2 - methylthio - 4 -amino-6-piperidino and 2-benzylthio-4-amino-6-piperidino. It is stated that R1 may also be ethyl, propyl, butyl or substituted benzyl and that R2 and/or R3 may be propyl, substituted phenyl or substituted benzyl; NR2R3 may also be morpholino. 2 - (Substituted mercapto) - 4 - amino - 6-halo-pyrimidines are made from 2-mercapto-4 - amino - 6 - hydroxypyrimidine by alkylation or aralkylation of the mercapto group and replacement of the hydroxyl by halogen. An example is given of the preparation of the 2-benzylmercapto compound.
GB26313/53A 1952-10-29 1953-09-24 Improvements relating to 2-substituted-mercapto-4-amino-6-disubstituted-aminopyrimidines and acid addition salts thereof Expired GB744867A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US744867XA 1952-10-29 1952-10-29

Publications (1)

Publication Number Publication Date
GB744867A true GB744867A (en) 1956-02-15

Family

ID=22119812

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26313/53A Expired GB744867A (en) 1952-10-29 1953-09-24 Improvements relating to 2-substituted-mercapto-4-amino-6-disubstituted-aminopyrimidines and acid addition salts thereof

Country Status (1)

Country Link
GB (1) GB744867A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073328A1 (en) * 1981-08-20 1983-03-09 LPB Istituto Farmaceutico s.p.a. Novel pyrimidine and s. triazine derivatives with antilipidemic activity
WO1995013267A1 (en) * 1993-11-12 1995-05-18 The Upjohn Company Pyrimidine-thioalkyl and alkylether compounds
US6043248A (en) * 1995-05-08 2000-03-28 Pharmacia & Upjohn Company Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as inhibitors of viral reverse transcriptase
US6124306A (en) * 1997-09-25 2000-09-26 Pharmacia & Upjohn Company Thioalkyl alpha substituted pyrimidine compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073328A1 (en) * 1981-08-20 1983-03-09 LPB Istituto Farmaceutico s.p.a. Novel pyrimidine and s. triazine derivatives with antilipidemic activity
WO1995013267A1 (en) * 1993-11-12 1995-05-18 The Upjohn Company Pyrimidine-thioalkyl and alkylether compounds
US5981537A (en) * 1993-11-12 1999-11-09 Pharmacia & Upjohn Company Pyrimidine-thioalkyl and alkylether compounds
EP1247804A1 (en) * 1993-11-12 2002-10-09 PHARMACIA &amp; UPJOHN COMPANY Pyrimidine-thioalkyl and alkylether compounds
US6043248A (en) * 1995-05-08 2000-03-28 Pharmacia & Upjohn Company Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as inhibitors of viral reverse transcriptase
US6124306A (en) * 1997-09-25 2000-09-26 Pharmacia & Upjohn Company Thioalkyl alpha substituted pyrimidine compounds

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