GB951652A - Sulphamyl triazolopyrimidines and their preparation - Google Patents

Sulphamyl triazolopyrimidines and their preparation

Info

Publication number
GB951652A
GB951652A GB2263660A GB2263660A GB951652A GB 951652 A GB951652 A GB 951652A GB 2263660 A GB2263660 A GB 2263660A GB 2263660 A GB2263660 A GB 2263660A GB 951652 A GB951652 A GB 951652A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkyl
preparation
formula
interaction
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
GB2263660A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2263660A priority Critical patent/GB951652A/en
Publication of GB951652A publication Critical patent/GB951652A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Abstract

The invention comprises compounds of general formula: <FORM:0951652/C2/1> wherein R1 and R2 are alkyl radicals, wherein of X and Y one is nitrogen and the other is a radical -CH=, and wherein R3 is hydrogen or alkyl and R4 is hydrogen, alkyl or phenyl; and their preparation by the interaction of an amine HNR3R4 in an inert diluent or solvent with a heterocyclic sulphonyl halide of formula: <FORM:0951652/C2/2> which may be prepared by the interaction of a mercapto compound of formula: <FORM:0951652/C2/3> with a halogen in an aqueous diluent or solvent. Mercapto compounds above are prepared by reacting carbon disulphide with an appropriate 2- or 6-hydrazinopyrimidine. According to the Provisional Specification R1, R2, R3 and R4 may be hydrocarbon radicals and the sulphonyl halides are obtained by halogenation of the mercapto compounds. The compounds of the invention have diuretic and anticonvulsive properties.
GB2263660A 1960-06-28 1960-06-28 Sulphamyl triazolopyrimidines and their preparation Expired GB951652A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2263660A GB951652A (en) 1960-06-28 1960-06-28 Sulphamyl triazolopyrimidines and their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2263660A GB951652A (en) 1960-06-28 1960-06-28 Sulphamyl triazolopyrimidines and their preparation

Publications (1)

Publication Number Publication Date
GB951652A true GB951652A (en) 1964-03-11

Family

ID=10182642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2263660A Expired GB951652A (en) 1960-06-28 1960-06-28 Sulphamyl triazolopyrimidines and their preparation

Country Status (1)

Country Link
GB (1) GB951652A (en)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0142152A2 (en) * 1983-11-14 1985-05-22 The Dow Chemical Company Novel substituted 1,2,4-triazolo- [1,5-a] pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil
EP0142811A2 (en) * 1983-11-14 1985-05-29 The Dow Chemical Company Method of preparing 1,2,4-triazolo [1,5-a] - pyrimidine-2-sulfonyl chlorides
EP0244948A2 (en) * 1986-04-30 1987-11-11 Schering Agrochemicals Limited Triazolopyrimidine herbicides
EP0256396A1 (en) * 1986-08-13 1988-02-24 Bayer Ag Triazolo-pyrimidine-2-sulfon amides
US4731446A (en) * 1987-05-01 1988-03-15 The Dow Chemical Company Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides
EP0297490A1 (en) * 1987-07-01 1989-01-04 Schering Aktiengesellschaft 6,7-Dihydro-pyrazolo[1,5-a][1,3,5]triazine-2-sulfonamides, processes for their preparation and their use as herbicides and plant growth regulators
US4799952A (en) * 1987-05-01 1989-01-24 The Dow Chemical Company Herbicidal imidazolo(1,2-a)pyrimidine-2-sulfonanilides
US4818273A (en) * 1983-11-14 1989-04-04 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides
EP0343752A1 (en) * 1988-05-25 1989-11-29 DowElanco Alkoxy-1,2,4-triazolo (1,5-c) pyrimidine-2-sulfonamides, process for their preparation and intermediates
US4886883A (en) * 1983-11-14 1989-12-12 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides
US4904301A (en) * 1988-04-19 1990-02-27 The Dow Chemical Company 5-Fluoromethyl-1,2,4-triazolo(1,5-A)-pyrimidines
US4910306A (en) * 1987-11-09 1990-03-20 The Dow Chemical Company Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides
US4954163A (en) * 1983-11-14 1990-09-04 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides
US4959473A (en) * 1988-04-19 1990-09-25 The Dow Chemical Company 7-ethoxy-5-fluoromethyl-1,2,4-triazole[1,5-a]-pyrimidine-2-sulfonamindes
US4960455A (en) * 1988-03-11 1990-10-02 Bayer Aktiengesellschaft Herbicidal triazolodihydropyrimidine-2-sulphonamides
US4979981A (en) * 1988-04-19 1990-12-25 The Dow Chemical Company 5-fluoromethyl-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonamides
US4992091A (en) * 1986-07-11 1991-02-12 The Dow Chemical Company Substituted pyrazolo[1,5-a]pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation
US4997940A (en) * 1986-07-11 1991-03-05 The Dow Chemical Company Pyrazolo[1,5-a]pyrimidine-2-sulfonyl chloride and -2-sulfide compounds
US5003096A (en) * 1989-05-30 1991-03-26 The Dow Chemical Company Preparation of substituted 1,2,4-triazolo[1,4-a]pyrimidine-2-sulfonanilides
US5015286A (en) * 1988-04-19 1991-05-14 The Dow Chemical Company 7-ethoxy-5-fluoromethyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides
US5021591A (en) * 1986-07-11 1991-06-04 The Dow Chemical Company Pyrazolo[1,5-a]pyrimidine-2-sulfide compounds
US5041157A (en) * 1989-01-11 1991-08-20 Ciba-Geigy Corporation 1,2,4-triazolo[1,5-A]pyridimidin-2-ylsulfonyl-3-aminothiophene-2-carboxylic esters as antidotes for certain herbicides
US5071468A (en) * 1988-12-23 1991-12-10 Shell Internationale Research Maatschappij B.V. Triazolopyrimidine herbicides
US5201938A (en) * 1991-07-19 1993-04-13 Dowelanco N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
US5217973A (en) * 1991-07-05 1993-06-08 Laboratoires Upsa Triazolopyrimidine derivatives which are angiotensin ii receptor antagonists processes for preparing them and pharmaceutical compositions containing them
US5461153A (en) * 1993-11-05 1995-10-24 Dowelanco 2-alkoxy-4-hydrazinopyrimidine compounds
US5480991A (en) * 1993-11-05 1996-01-02 Dowelanco 2-Alkoxy-4-hydroazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds
US5488109A (en) * 1993-11-05 1996-01-30 Dowelanco 5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)--thione compounds and their use in the preparation of and 2-chlorosulfonyl-5-alkoxy[1,2,4]triazolo[1,5-c]-pyrimidine compounds
US5571775A (en) * 1994-07-11 1996-11-05 Dowelanco N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides
US6680388B2 (en) 2000-06-16 2004-01-20 Bayer Cropscience Ag Method for preparing substituted 5-amino-N-phenyl-1,2,4-triazole-3-sulfonamides
EP1430898A1 (en) * 2001-09-28 2004-06-23 Kyowa Hakko Kogyo Co., Ltd. Receptor antagonist

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU583799B2 (en) * 1983-11-14 1989-05-11 Dow Chemical Company, The Novel substituted 1,2,4-triazolo-(1,5-a)pyrimidine-2- sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil
US4818273A (en) * 1983-11-14 1989-04-04 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides
EP0142152A2 (en) * 1983-11-14 1985-05-22 The Dow Chemical Company Novel substituted 1,2,4-triazolo- [1,5-a] pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil
EP0142811A3 (en) * 1983-11-14 1986-03-12 The Dow Chemical Company Method of preparing 1,2,4-triazolo [1,5-a] - pyrimidine-2-sulfonyl chlorides
EP0142152A3 (en) * 1983-11-14 1986-10-01 The Dow Chemical Company Novel substituted 1,2,4-triazolo- û1,5-a¨ pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil
US4886883A (en) * 1983-11-14 1989-12-12 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides
EP0142811A2 (en) * 1983-11-14 1985-05-29 The Dow Chemical Company Method of preparing 1,2,4-triazolo [1,5-a] - pyrimidine-2-sulfonyl chlorides
US4755212A (en) * 1983-11-14 1988-07-05 The Dow Chemical Company Novel substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides and compositions and method for inhibiting pollen formation in corn
US4954163A (en) * 1983-11-14 1990-09-04 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides
US4741764A (en) * 1983-11-14 1988-05-03 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and inhibiting sugar beet bolting
US4983772A (en) * 1983-11-14 1991-01-08 The Dow Chemical Company 2,6-disubstituted anilines
GB2149792A (en) * 1983-11-14 1985-06-19 Dow Chemical Co Novel n-aryl substituted 1,2,4-triazolo1,5-a-pyrimidine-2-sulfonamidess
US4740233A (en) * 1983-11-14 1988-04-26 The Dow Chemical Company Substituted 1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil
EP0244948A2 (en) * 1986-04-30 1987-11-11 Schering Agrochemicals Limited Triazolopyrimidine herbicides
EP0244948A3 (en) * 1986-04-30 1989-03-15 Schering Agrochemicals Limited Triazolopyrimidine herbicides
US4992091A (en) * 1986-07-11 1991-02-12 The Dow Chemical Company Substituted pyrazolo[1,5-a]pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation
US4997940A (en) * 1986-07-11 1991-03-05 The Dow Chemical Company Pyrazolo[1,5-a]pyrimidine-2-sulfonyl chloride and -2-sulfide compounds
US5021591A (en) * 1986-07-11 1991-06-04 The Dow Chemical Company Pyrazolo[1,5-a]pyrimidine-2-sulfide compounds
EP0256396A1 (en) * 1986-08-13 1988-02-24 Bayer Ag Triazolo-pyrimidine-2-sulfon amides
US4854964A (en) * 1986-08-13 1989-08-08 Bayer Aktiengesellschaft Triazolo-pyrimidine-2-sulphonamides having herbicidal utility
US4799952A (en) * 1987-05-01 1989-01-24 The Dow Chemical Company Herbicidal imidazolo(1,2-a)pyrimidine-2-sulfonanilides
US4731446A (en) * 1987-05-01 1988-03-15 The Dow Chemical Company Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides
EP0297490A1 (en) * 1987-07-01 1989-01-04 Schering Aktiengesellschaft 6,7-Dihydro-pyrazolo[1,5-a][1,3,5]triazine-2-sulfonamides, processes for their preparation and their use as herbicides and plant growth regulators
US4892576A (en) * 1987-07-01 1990-01-09 Schering Aktiengesellschaft 6,7-dihydro-pyrazolo (1,5-A)(1,3,5)triazine-2-sulphonamides, processes for their preparation and their use as herbicides and plant growth regulators
US4910306A (en) * 1987-11-09 1990-03-20 The Dow Chemical Company Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides
US4960455A (en) * 1988-03-11 1990-10-02 Bayer Aktiengesellschaft Herbicidal triazolodihydropyrimidine-2-sulphonamides
US4979981A (en) * 1988-04-19 1990-12-25 The Dow Chemical Company 5-fluoromethyl-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonamides
US4904301A (en) * 1988-04-19 1990-02-27 The Dow Chemical Company 5-Fluoromethyl-1,2,4-triazolo(1,5-A)-pyrimidines
US5015286A (en) * 1988-04-19 1991-05-14 The Dow Chemical Company 7-ethoxy-5-fluoromethyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides
US4959473A (en) * 1988-04-19 1990-09-25 The Dow Chemical Company 7-ethoxy-5-fluoromethyl-1,2,4-triazole[1,5-a]-pyrimidine-2-sulfonamindes
US5163995A (en) * 1988-05-25 1992-11-17 Dowelanco Herbicidal alkoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamides
US5010195A (en) * 1988-05-25 1991-04-23 The Dow Chemical Company Herbicidal alkoxy-1,2,4-triazolo(1,5-c)primidine-2-sulfonamides
EP0343752A1 (en) * 1988-05-25 1989-11-29 DowElanco Alkoxy-1,2,4-triazolo (1,5-c) pyrimidine-2-sulfonamides, process for their preparation and intermediates
AU616519B2 (en) * 1988-05-25 1991-10-31 Dow Chemical Company, The Alkoxy-1,2,4-triazolo(1,5-c)pyrimidine-2-sulfonamides, process for their preparation and intermediates
US5071468A (en) * 1988-12-23 1991-12-10 Shell Internationale Research Maatschappij B.V. Triazolopyrimidine herbicides
US5041157A (en) * 1989-01-11 1991-08-20 Ciba-Geigy Corporation 1,2,4-triazolo[1,5-A]pyridimidin-2-ylsulfonyl-3-aminothiophene-2-carboxylic esters as antidotes for certain herbicides
US5003096A (en) * 1989-05-30 1991-03-26 The Dow Chemical Company Preparation of substituted 1,2,4-triazolo[1,4-a]pyrimidine-2-sulfonanilides
US5217973A (en) * 1991-07-05 1993-06-08 Laboratoires Upsa Triazolopyrimidine derivatives which are angiotensin ii receptor antagonists processes for preparing them and pharmaceutical compositions containing them
US5201938A (en) * 1991-07-19 1993-04-13 Dowelanco N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
US5461153A (en) * 1993-11-05 1995-10-24 Dowelanco 2-alkoxy-4-hydrazinopyrimidine compounds
US5480991A (en) * 1993-11-05 1996-01-02 Dowelanco 2-Alkoxy-4-hydroazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds
US5488109A (en) * 1993-11-05 1996-01-30 Dowelanco 5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)--thione compounds and their use in the preparation of and 2-chlorosulfonyl-5-alkoxy[1,2,4]triazolo[1,5-c]-pyrimidine compounds
US5571775A (en) * 1994-07-11 1996-11-05 Dowelanco N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides
US6680388B2 (en) 2000-06-16 2004-01-20 Bayer Cropscience Ag Method for preparing substituted 5-amino-N-phenyl-1,2,4-triazole-3-sulfonamides
EP1430898A1 (en) * 2001-09-28 2004-06-23 Kyowa Hakko Kogyo Co., Ltd. Receptor antagonist
EP1430898A4 (en) * 2001-09-28 2005-11-02 Kyowa Hakko Kogyo Kk Receptor antagonist

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