ES2005441A6 - 2-Guanidino thiazole deriv. prodn. - Google Patents

2-Guanidino thiazole deriv. prodn.

Info

Publication number
ES2005441A6
ES2005441A6 ES8703223A ES8703223A ES2005441A6 ES 2005441 A6 ES2005441 A6 ES 2005441A6 ES 8703223 A ES8703223 A ES 8703223A ES 8703223 A ES8703223 A ES 8703223A ES 2005441 A6 ES2005441 A6 ES 2005441A6
Authority
ES
Spain
Prior art keywords
cyclisation
obtd
thiourea
catalyst
formula
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
ES8703223A
Other languages
Spanish (es)
Inventor
Peter Bod
Kalman Harsanyi
Csonger Eva Againe
Ferenc Trischler
Erik Bogsch
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.)
Richter Gedeon Nyrt
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Nyrt
Richter Gedeon Vegyeszeti Gyar RT
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 Richter Gedeon Nyrt, Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Nyrt
Publication of ES2005441A6 publication Critical patent/ES2005441A6/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Produced 2-guanidino- 4-amidino- thiomethyl thiazole has formula (I). Cpd. (I) is obtd. by cyclisation of amidino-thiourea of formula (II) with 1,3-dihaloacetone, in an organic solvent, followed by reacting the cyclisation prod. of formula (III) (where X is halide ion), with thiourea in the presence of water, with heating, and conversion of obtd. dihydrohalide of (I) into a free base. Cyclisation is conducted in presence of catalyst comprising alkali metal (pref. sodium) iodide, using aliphatic 3-6C ketone (pref. acetone) or aliphatic 2-4C nitrile as solvent, in which the catalyst is dissolved. The reaction temp. is 20-40 deg.C. Prod. of cyclisation (III) is reacted with thiourea directly in the reaction mixt. obtd. at cyclisation stage. Alkali metal iodide (catalyst) is taken in amt. 4-6 mol.%. The yield of (I) is 85-90% and the content of biologically active substance is up to
ES8703223A 1986-11-12 1987-11-12 2-Guanidino thiazole deriv. prodn. Expired ES2005441A6 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU864658A HU195959B (en) 1986-11-12 1986-11-12 Process for producing 2-guanidino-thiazole derivatives

Publications (1)

Publication Number Publication Date
ES2005441A6 true ES2005441A6 (en) 1989-03-01

Family

ID=10968597

Family Applications (1)

Application Number Title Priority Date Filing Date
ES8703223A Expired ES2005441A6 (en) 1986-11-12 1987-11-12 2-Guanidino thiazole deriv. prodn.

Country Status (14)

Country Link
KR (1) KR900006556B1 (en)
AR (1) AR243874A1 (en)
AT (1) AT389510B (en)
CA (1) CA1323032C (en)
CS (1) CS268693B2 (en)
DK (1) DK169966B1 (en)
ES (1) ES2005441A6 (en)
FI (1) FI84912C (en)
GR (1) GR871696B (en)
HU (1) HU195959B (en)
NO (1) NO167387C (en)
PT (1) PT86113B (en)
SU (1) SU1678205A3 (en)
YU (1) YU46086B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5731442A (en) * 1997-03-11 1998-03-24 Albemarle Corporation Synthesis of thiazole derivatives
US5856500A (en) * 1997-03-11 1999-01-05 Albemarle Corporation Synthesis of thiazole derivatives

Also Published As

Publication number Publication date
HU195959B (en) 1988-08-29
DK587287D0 (en) 1987-11-10
SU1678205A3 (en) 1991-09-15
AR243874A1 (en) 1993-09-30
DK169966B1 (en) 1995-04-18
KR900006556B1 (en) 1990-09-13
NO167387C (en) 1991-10-30
CA1323032C (en) 1993-10-12
GR871696B (en) 1987-12-08
CS810187A2 (en) 1989-07-12
FI84912B (en) 1991-10-31
NO167387B (en) 1991-07-22
NO874698L (en) 1988-05-13
KR890008120A (en) 1989-07-08
PT86113B (en) 1990-08-31
DK587287A (en) 1988-05-13
ATA277087A (en) 1989-05-15
NO874698D0 (en) 1987-11-11
PT86113A (en) 1987-12-01
YU204987A (en) 1988-10-31
CS268693B2 (en) 1990-04-11
FI84912C (en) 1992-02-10
AT389510B (en) 1989-12-27
FI875003A0 (en) 1987-11-12
FI875003A (en) 1988-06-13
YU46086B (en) 1992-12-21

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Legal Events

Date Code Title Description
SA6 Expiration date (snapshot 920101)

Free format text: 2007-11-12

FD1A Patent lapsed

Effective date: 20071113