GB1112128A - New thiazolyl-diphenylmethane derivatives - Google Patents

New thiazolyl-diphenylmethane derivatives

Info

Publication number
GB1112128A
GB1112128A GB5448565A GB5448565A GB1112128A GB 1112128 A GB1112128 A GB 1112128A GB 5448565 A GB5448565 A GB 5448565A GB 5448565 A GB5448565 A GB 5448565A GB 1112128 A GB1112128 A GB 1112128A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
thiazolyl
reacting
carbon atoms
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
GB5448565A
Inventor
Marcel Pesson
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.)
Laboratoire Roger Bellon SA
Original Assignee
Laboratoire Roger Bellon 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 Laboratoire Roger Bellon SA filed Critical Laboratoire Roger Bellon SA
Priority to GB5448565A priority Critical patent/GB1112128A/en
Priority to FR1601733D priority patent/FR1601733A/en
Priority to FR88356A priority patent/FR5839M/fr
Publication of GB1112128A publication Critical patent/GB1112128A/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
    • C07D277/24—Radicals substituted by oxygen 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1112128/C4-C5/1> where R3 is hydroxy, alkoxy of 1-4 carbon atoms or acyloxy and R1 and R2 are hydrogen, alkyl of 1-4 carbon atoms mononuclear aryl of a N-containing ring, or R1 and R2 form an alkylene chain of up to 4 carbon atoms. The compounds may be prepared (a) by condensing an a -halogenated ketone of the formula R1-CO-CHX-R2 where X is halogen, with a 4,41-dialkoxy-diphenyl thioacetamide; (b) by reacting two mols. of a p-alkoxyphenyl magnesium bromide with a compound of the formula <FORM:1112128/C4-C5/2> to give a carbinol which is then reduced; (c) by reacting a compound of the formula <FORM:1112128/C4-C5/3> with a 4,41-dialkoxybenzophenone and reducing the carbinol formed; (d) by reacting a tertiary amide of an acid of the formula <FORM:1112128/C4-C5/4> with two mols. of p-alkoxyphenyl magnesium bromide and reducing the carbinol formed; and (e) condensing the sodium derivative of 4,41-dialkoxy diphenyl acetonitrile with a compound of the formula <FORM:1112128/C4-C5/5> where X is halogen, to give a bis (p-alkoxyphenyl) - (2 - thiazolyl) - acetonitrile which is dealkylated and hydrolysed with 48% HBr in acetic acid to give bis (p-hydroxyphenyl)-(2-thiazolyl)-acetamide, the saponification of which with KOH accompanied by decarboxylation gives bis (p - hydroxyphenyl) - (2 - thiazolyl)-methane. The compounds wherein R3 is OH may be prepared by dealkylating the alkoxy derivatives, and those wherein R3 is acyloxy may be prepared by acylating the hydroxy compounds.ALSO:The invention comprises compounds of the formula <FORM:1112128/C2/1> where R3 is hydroxy, alkoxy of 1-4 carbon atoms or acyloxy and R1 and R2 are hydrogen, alkyl of 1-4 carbon atoms mononuclear aryl of a N-containing ring, or R1 and R2 form an alkylene chain of up to 4 carbon atoms. The compounds may be prepared (a) by condensing an a -halogenated ketone of the formula R1-CO-CHX-R2 where X is halogen, with a 4,41-dialkoxy-diphenyl thiocetamide, (b) by reacting two mols of a p-alkoxy-phenyl magnesium bromide with a compound of the formula <FORM:1112128/C2/2> to give a carbinol which is then reduced, (c) by reacting a compound of the formula <FORM:1112128/C2/3> with a 4,41-dialkoxybenzophenone and reducing the carbinol formed, (d) by reacting a tertiary amide of an acid of the formula <FORM:1112128/C2/4> with two mols of p-alkoxyphenyl magnesium bromide and reducing the carbinol formed and (e) condensing the sodium derivative of 4,41-dialkoxy diphenyl acetonitrile with a compound of the formula <FORM:1112128/C2/5> where X is halogen, to give a bis(p-alkoxy-phenyl) -(2-thiazolyl)-acetonitrile which is dealkylated and hydrolysed with 48% HBr in acetic acid to give bis(p-hydroxyphenyl)-(2-thiazolyl)-acetamide the saponification of which with KOH accompanied by decarboxylation gives bis(p-hydroxyphenyl) - (2 - thiazolyl) - methane. The compounds wherein R3 is OH may be prepared by dealkylating the alkoxy derivatives, and those wherein R3 is acyloxy may be prepared by acylating the hydroxy compounds. Certain of the compounds may be used in pharmaceutical compositions.
GB5448565A 1965-12-22 1965-12-22 New thiazolyl-diphenylmethane derivatives Expired GB1112128A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB5448565A GB1112128A (en) 1965-12-22 1965-12-22 New thiazolyl-diphenylmethane derivatives
FR1601733D FR1601733A (en) 1965-12-22 1966-12-21 2-thiazolyl diphenylmethane derivs laxatives
FR88356A FR5839M (en) 1965-12-22 1966-12-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5448565A GB1112128A (en) 1965-12-22 1965-12-22 New thiazolyl-diphenylmethane derivatives

Publications (1)

Publication Number Publication Date
GB1112128A true GB1112128A (en) 1968-05-01

Family

ID=10471157

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5448565A Expired GB1112128A (en) 1965-12-22 1965-12-22 New thiazolyl-diphenylmethane derivatives

Country Status (2)

Country Link
FR (2) FR5839M (en)
GB (1) GB1112128A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0149884A2 (en) * 1983-09-09 1985-07-31 Takeda Chemical Industries, Ltd. 5-Pyridyl-1,3-thiazole derivatives, their production and use
JPS6137784A (en) * 1984-07-25 1986-02-22 メルク　エンド　カムパニー　インコーポレーテツド 2_benzyl_4_(4_pyridyl)thiazoles and derivatives as immunoregulator

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE7694T1 (en) * 1980-02-14 1984-06-15 Grigg, Ronald Ernest DERIVATIVES OF 2-METHYL-5-THIAZOLMETHYLAMINE AND CARBOXAMIDE.
GB9027613D0 (en) * 1990-12-20 1991-02-13 Ici Plc Fungicides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0149884A2 (en) * 1983-09-09 1985-07-31 Takeda Chemical Industries, Ltd. 5-Pyridyl-1,3-thiazole derivatives, their production and use
EP0149884A3 (en) * 1983-09-09 1986-07-30 Takeda Chemical Industries, Ltd. 5-pyridyl-1,3-thiazole derivatives, their production and use
JPS6137784A (en) * 1984-07-25 1986-02-22 メルク　エンド　カムパニー　インコーポレーテツド 2_benzyl_4_(4_pyridyl)thiazoles and derivatives as immunoregulator

Also Published As

Publication number Publication date
FR5839M (en) 1968-04-10
FR1601733A (en) 1970-09-14

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