GB1148629A - s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group - Google Patents

s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group

Info

Publication number
GB1148629A
GB1148629A GB5680866A GB5680866A GB1148629A GB 1148629 A GB1148629 A GB 1148629A GB 5680866 A GB5680866 A GB 5680866A GB 5680866 A GB5680866 A GB 5680866A GB 1148629 A GB1148629 A GB 1148629A
Authority
GB
United Kingdom
Prior art keywords
substituted
group
amino
compound
triazolo
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
GB5680866A
Inventor
Ernst Tenor
Heinz Fuller
Fritz Hausschild
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.)
Deutsches Hydrierwerk Rodleben VEB
Original Assignee
Deutsches Hydrierwerk Rodleben VEB
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 Deutsches Hydrierwerk Rodleben VEB filed Critical Deutsches Hydrierwerk Rodleben VEB
Publication of GB1148629A publication Critical patent/GB1148629A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,148,629. s - Triazolo - [1,5 - a] - pyrimidines. DEUTSCHES HYDRIERWERK RODLEBEN VEB. 19 Dec., 1966, No. 56808/66. Heading C2C. s-Triazolo-[1,5-a]-pyrimidines I of Formula I, in which each of R 1 and R 4 is a hydrogen or halogen atom or a C 1-4 alkyl or alkoxyalkyl group or an aralkyl or aryl group which may be substituted in the nucleus, R 2 is a hydrogen or halogen atom or a C 1-4 alkyl, alkenyl, aralkyl or aryl group and R 3 is a free amino group, an amino group substituted by one or two alkyl, cycloalkyl, alkenyl, hydroxyalkyl, alkylaminoalkyl, alkoxy, heterocyclic or possibly substituted aryl or aralkyl groups, or R 3 is a hydrazino, guanidino, tertiary cyclic amino or basically-substituted, straight or branched chain C 2-4 alkoxy group, the basic group being any one of the aforementioned amino, substitutedamino, guanidino, hydrazino or cyclic amino groups, are prepared by (a) reacting a compound II of Formula II, in which R is a halogen atom or a mercapto, alkylthio or alkoxy group with a compound of formula R 3 H, in which R 3 is an amino, substituted-amino, hydrazino, guanidino or tertiary cyclic amino group, to give the compounds I in which R 3 is as defined immediately above, or (b) reacting a compound II, in which R is a chlorine or bromine atom, with the sodium compound of an appropriate basically-substituted alkanol, to give the compounds I in which R 3 is a basically-substituted C 2-4 alkoxy group. The compounds I have a coronary vasodilative effect.
GB5680866A 1966-10-03 1966-12-19 s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group Expired GB1148629A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEV0032057 1966-10-03

Publications (1)

Publication Number Publication Date
GB1148629A true GB1148629A (en) 1969-04-16

Family

ID=7586955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5680866A Expired GB1148629A (en) 1966-10-03 1966-12-19 s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group

Country Status (2)

Country Link
DE (1) DE1620694C3 (en)
GB (1) GB1148629A (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4209621A (en) * 1979-04-27 1980-06-24 American Cyanamid Company (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines
US4567263A (en) * 1981-08-01 1986-01-28 Basf Aktiengesellschaft 7-Aminoazolo[1,5-a]-pyrimidines and fungicides containing these compounds
US4617303A (en) * 1983-10-21 1986-10-14 Basf Aktiengesellschaft 7-aminoazolo[1,5-a]pyrimidines and fungicides containing these
US5478825A (en) * 1991-02-22 1995-12-26 Egis Gyogyszergyar 5-(substituted amino)-1,2,4-triazolo (1,5-A) pyrimidine derivatives
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
US6277857B1 (en) * 1998-09-25 2001-08-21 American Cyanamid Company Fungicidal 7-oxy-and 7-thio-substituted-triazolopyrimidines
US6369065B1 (en) 2000-05-15 2002-04-09 Ucb S.A. CD40 signal blocking agent
WO2003039259A1 (en) * 2001-11-08 2003-05-15 Syngenta Limited Fungicides
WO2005087773A1 (en) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087772A1 (en) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2006092428A2 (en) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound
US7501383B2 (en) 2004-03-10 2009-03-10 Basf Aktiengesellschaft Substituted [1,2,4]triazolo[1,5-a]pyrimidines and their use for controlling harmful fungi
US8664235B2 (en) 2003-09-12 2014-03-04 Merial Limited 6-Halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests
CN104610266A (en) * 2015-01-14 2015-05-13 湖北美林药业有限公司 Trapidil compound and pharmaceutical composition thereof
US10357481B2 (en) * 2015-07-01 2019-07-23 Merck Sharp & Dohme Corp. Substituted triazolo bicyclic compounds as PDE2 inhibitors

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3533050A1 (en) * 1985-09-17 1987-03-26 Basf Ag 7-AMINO-AZOLO (1,5-A) PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM, OR THEIR USE AS FUNGICIDES
DE3627411A1 (en) * 1986-08-13 1988-02-18 Bayer Ag TRIAZOLO-PYRIMIDINE-2-SULPHONAMIDE
ES2308726T3 (en) * 2005-02-16 2008-12-01 Basf Se 5-ALCOXIAQUIL-6-ALQUIL-7-AMINO-AZOLOPIRIMIDINAS, PROCEDURE FOR ITS OBTAINING AND ITS EMPLOYMENT FOR THE FIGHT AGAINST DAMAGING FUNGES AS WELL AS AGENTS CONTAINING THEM.

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4209621A (en) * 1979-04-27 1980-06-24 American Cyanamid Company (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines
US4567263A (en) * 1981-08-01 1986-01-28 Basf Aktiengesellschaft 7-Aminoazolo[1,5-a]-pyrimidines and fungicides containing these compounds
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines
US4617303A (en) * 1983-10-21 1986-10-14 Basf Aktiengesellschaft 7-aminoazolo[1,5-a]pyrimidines and fungicides containing these
USRE32676E (en) * 1983-10-21 1988-05-24 Basf Aktiengesellschaft 7-aminozolo[1,5-a]pyrimidines and fungicides containing these
US5478825A (en) * 1991-02-22 1995-12-26 Egis Gyogyszergyar 5-(substituted amino)-1,2,4-triazolo (1,5-A) pyrimidine derivatives
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
US6277857B1 (en) * 1998-09-25 2001-08-21 American Cyanamid Company Fungicidal 7-oxy-and 7-thio-substituted-triazolopyrimidines
US6369065B1 (en) 2000-05-15 2002-04-09 Ucb S.A. CD40 signal blocking agent
WO2003039259A1 (en) * 2001-11-08 2003-05-15 Syngenta Limited Fungicides
US8664235B2 (en) 2003-09-12 2014-03-04 Merial Limited 6-Halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests
WO2005087773A1 (en) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
EA009883B1 (en) * 2004-03-10 2008-04-28 Басф Акциенгезельшафт 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
EA010411B1 (en) * 2004-03-10 2008-08-29 Басф Акциенгезельшафт 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
US7501383B2 (en) 2004-03-10 2009-03-10 Basf Aktiengesellschaft Substituted [1,2,4]triazolo[1,5-a]pyrimidines and their use for controlling harmful fungi
WO2005087772A1 (en) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
US9487519B2 (en) 2004-03-10 2016-11-08 Basf Se 5,6-Dialkyl-7-aminotriazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
WO2006092428A2 (en) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound
WO2006092428A3 (en) * 2005-03-02 2006-11-30 Basf Ag 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound
CN104610266A (en) * 2015-01-14 2015-05-13 湖北美林药业有限公司 Trapidil compound and pharmaceutical composition thereof
US10357481B2 (en) * 2015-07-01 2019-07-23 Merck Sharp & Dohme Corp. Substituted triazolo bicyclic compounds as PDE2 inhibitors

Also Published As

Publication number Publication date
DE1620694A1 (en) 1970-12-03
DE1620694B2 (en) 1981-07-16
DE1620694C3 (en) 1982-04-15

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