GB1110099A - Urea and thiourea derivatives - Google Patents

Urea and thiourea derivatives

Info

Publication number
GB1110099A
GB1110099A GB25356/66A GB2535666A GB1110099A GB 1110099 A GB1110099 A GB 1110099A GB 25356/66 A GB25356/66 A GB 25356/66A GB 2535666 A GB2535666 A GB 2535666A GB 1110099 A GB1110099 A GB 1110099A
Authority
GB
United Kingdom
Prior art keywords
formula
treating
reacting
prepared
urea
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
GB25356/66A
Inventor
Marc Julia
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
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 Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB1110099A publication Critical patent/GB1110099A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel urea and thiourea derivatives of Formula I <FORM:1110099/C2/1> wherein X is oxygen or sulphur, A is a straight or branched alkylene group having 1-4 carbon atoms, the groups -NH- and -CO-attached to a common benzene nucleus are in meta or para position in relation to one another, R and R1 are hydrogen or methyl, and the groupings -NH- and -CH3 attached to a common benzene nucleus are in ortho position in relation to one another, and acid addition salts thereof, are prepared by reacting two moles of an amino-amidine of Formula II <FORM:1110099/C2/2> or an acid addition salt thereof, with one mole of carbonyldiimidazole or thiocarbonyldiimidazole, with or without an inert and anhydrous organic solvent at a temperature between ambient and 120 DEG C., or by reacting one mole of a 1,3-bis-(3-chlorocarbonylphenyl)-urea or -thiourea with two moles of an aminoamidine of formula <FORM:1110099/C2/3> and, in each case, optionally converting the product obtained into an acid addition salt. The starting materials of Formula II may be prepared by the series of reactions shown in the following reaction scheme: <FORM:1110099/C2/4> The bis(3-chlorocarbonylphenyl)-ureas or thioureas may be prepared by treating the corresponding diacid obtained by reacting amino-benzoic acid with urea, with thionyl chloride. The amidines of Formula II may also be prepared by treating a (nitrobenzamido)-benzoic acid with thionyl chloride, reacting the acid chloride with an aminonitrile, treating the [(nitrobenzamido)-benzamido]-nitrile with dry gaseous hydrogen chloride in chloroform/ethanol, isolating the imino-ether hydrochloride and treating this with anhydrous ammonia at 0 DEG C. to give the [(nitrobenzamido)benzamido]-amidine which is then hydrogenated. Therapeutic compositions having anti-viral and hepatoprotective activity, which may be administered parenterally, or orally, contain as active ingredient at least one compound of Formula I above or a non-toxic acid addition salt thereof.
GB25356/66A 1965-06-09 1966-06-07 Urea and thiourea derivatives Expired GB1110099A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR20072A FR1489720A (en) 1965-06-09 1965-06-09 New urea derivatives and their preparation
FR36783A FR89804E (en) 1965-06-09 1965-10-29 New urea derivatives and their preparation
FR60820 1966-05-09

Publications (1)

Publication Number Publication Date
GB1110099A true GB1110099A (en) 1968-04-18

Family

ID=27242225

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25356/66A Expired GB1110099A (en) 1965-06-09 1966-06-07 Urea and thiourea derivatives

Country Status (5)

Country Link
BE (1) BE682282A (en)
CH (1) CH453334A (en)
FR (4) FR1489720A (en)
GB (1) GB1110099A (en)
NL (1) NL6607601A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1714958A1 (en) * 2004-01-28 2006-10-25 Mitsui Chemicals, Inc. Amide derivatives, process for production of the same, and method for application thereof as insecticide
US7678811B2 (en) 2002-02-11 2010-03-16 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US8076488B2 (en) 2003-02-28 2011-12-13 Bayer Healthcare Llc Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8841330B2 (en) 1999-01-13 2014-09-23 Bayer Healthcare Llc Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8242147B2 (en) 2002-02-11 2012-08-14 Bayer Healthcare Llc Aryl ureas with angiogenisis inhibiting activity
US7678811B2 (en) 2002-02-11 2010-03-16 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US8618141B2 (en) 2002-02-11 2013-12-31 Bayer Healthcare Llc Aryl ureas with angiogenesis inhibiting activity
US8071616B2 (en) 2002-02-11 2011-12-06 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US8076488B2 (en) 2003-02-28 2011-12-13 Bayer Healthcare Llc Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
JP2010209073A (en) * 2004-01-28 2010-09-24 Mitsui Chemicals Agro Inc Amide derivative
AU2004315003B2 (en) * 2004-01-28 2011-11-17 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US8563736B2 (en) 2004-01-28 2013-10-22 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US8710234B2 (en) 2004-01-28 2014-04-29 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
EP1714958A1 (en) * 2004-01-28 2006-10-25 Mitsui Chemicals, Inc. Amide derivatives, process for production of the same, and method for application thereof as insecticide
US8168825B2 (en) 2004-01-28 2012-05-01 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US9185912B2 (en) 2004-01-28 2015-11-17 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
EP1714958B1 (en) * 2004-01-28 2016-12-21 Mitsui Chemicals Agro, Inc. Amide derivatives, process for production of the same, and method for application thereof as insecticide
US9920026B2 (en) 2004-01-28 2018-03-20 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US10435385B2 (en) 2004-01-28 2019-10-08 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US10995081B2 (en) 2004-01-28 2021-05-04 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide
US11760742B2 (en) 2004-01-28 2023-09-19 Mitsui Chemicals, Inc. Amide derivatives, process for preparation thereof and use thereof as insecticide

Also Published As

Publication number Publication date
BE682282A (en) 1966-12-08
FR1489720A (en) 1967-07-28
NL6607601A (en) 1966-12-12
FR89804E (en) 1967-08-25
CH453334A (en) 1968-06-14
FR90420E (en) 1968-02-21
FR4652M (en) 1966-12-05

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