GB925539A - Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives - Google Patents

Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives

Info

Publication number
GB925539A
GB925539A GB1914062A GB1914062A GB925539A GB 925539 A GB925539 A GB 925539A GB 1914062 A GB1914062 A GB 1914062A GB 1914062 A GB1914062 A GB 1914062A GB 925539 A GB925539 A GB 925539A
Authority
GB
United Kingdom
Prior art keywords
trifluoromethyl
give
benzoic acid
xanthene
xanthenones
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
GB1914062A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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
Priority claimed from US12966A external-priority patent/US3192204A/en
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB925539A publication Critical patent/GB925539A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes 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 in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

The invention comprises xanthene and thiaxanthene derivatives of the formula <FORM:0925539/IV(a)/1> wherein Y = S or O and P is -CH2- or -CO-, the trifluoromethyl group being preferably in the 2-position. The trifluoromethyl-thiaxanthenones are made by condensing 1-chloro-2-nitrotrifluoromethylbenzene with thiosalicylic acid to give o-(2-nitrotrifluoromethylphenylthio) benzoic acid, reducing the nitro group, e.g. with stannous chloride, diazotising the resulting amino compound and treating with ethanol and copper-bronze powder to give o-(trifluoromethylphenylthio) benzoic acid and cyclizing by refluxing with a mineral acid. The trifluoromethyl xanthenones are made by diazotising 2-chlorotrifluoromethylaniline and treating with potassium iodide to give chloro-iodo-trifluoromethylbenzene, replacing the iodine atom by a carboxyl group by Grignard reaction, condensing with phenol and dehydrating the resulting 2-phenoxytrifluoromethyl-benzoic acid. The trifluoromethyl-xanthene and thiaxanthene are made by reduction of the xanthenones or thiaxanthenones by catalytic hydrogenation, sodium and an alcohol or a metal hydride such as lithium aluminium hydride.
GB1914062A 1960-03-07 1961-03-03 Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives Expired GB925539A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12966A US3192204A (en) 1960-03-07 1960-03-07 Trifluoromethylthiaxanthene and -xanthene derivatives
US2693960A 1960-05-05 1960-05-05

Publications (1)

Publication Number Publication Date
GB925539A true GB925539A (en) 1963-05-08

Family

ID=26684247

Family Applications (2)

Application Number Title Priority Date Filing Date
GB793161A Expired GB925538A (en) 1960-03-07 1961-03-03 Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives
GB1914062A Expired GB925539A (en) 1960-03-07 1961-03-03 Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB793161A Expired GB925538A (en) 1960-03-07 1961-03-03 Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives

Country Status (5)

Country Link
BE (1) BE600735A (en)
DE (2) DE1210890B (en)
FR (1) FR1002M (en)
GB (2) GB925538A (en)
SE (1) SE333573B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518196A1 (en) * 1991-06-11 1992-12-16 E.I. Du Pont De Nemours And Company Polyethers based on 9,9-BIS-perfluoroalkyl-3,6-dihydroxy-xanthene or 9-aryl-9-perfluoroalkyl-3,6-dihydroxy-xanthene

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159636A (en) * 1963-07-05 1964-12-01 Searle & Co 1-amino-4-(xanthenyl and thioxanthenyl) piperazines
US3157658A (en) * 1963-07-05 1964-11-17 Searle & Co 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds
US5104858A (en) * 1988-09-29 1992-04-14 Yale University Sensitizing multidrug resistant cells to antitumor agents
ITMI20032024A1 (en) * 2003-10-17 2005-04-18 Laboratorio Chimico Int Spa PROCEDURE FOR THE PREPARATION OF Z-FLUPENTIXOL
CN1976723B (en) 2004-04-30 2010-12-29 Bkg制药有限公司 Use of preparing medicine for treating or preventing infectious diseases
MX2009007235A (en) 2007-01-05 2009-10-16 Bkg Pharma Aps Low-carbohydrate milk with original calcium.
EP2374450B8 (en) 2010-04-06 2012-10-17 H. Lundbeck A/S Flupentixol compositions
CN104693173B (en) * 2015-03-09 2018-03-27 广东帅广医药有限公司 Preparation method of flupentixol hydrochloride
CN107987053B (en) * 2017-12-08 2023-04-14 植恩生物技术股份有限公司 Preparation method of high-purity Z-type flupentixol hydrochloride

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1044103B (en) * 1956-06-12 1958-11-20 Hoffmann La Roche Process for the production of xanthene or thioxanthene derivatives
AT202152B (en) * 1956-12-28 1959-02-10 American Cyanamid Co Process for the preparation of new dimethylaminopropylidene thiaxanthenes.
AT202143B (en) * 1956-12-28 1959-02-10 American Cyanamid Co Process for the preparation of new dimethylaminopropylidenexanthenes
FR1173489A (en) * 1957-04-04 1959-02-25 Merck & Co Inc Substituted thiaxanthenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518196A1 (en) * 1991-06-11 1992-12-16 E.I. Du Pont De Nemours And Company Polyethers based on 9,9-BIS-perfluoroalkyl-3,6-dihydroxy-xanthene or 9-aryl-9-perfluoroalkyl-3,6-dihydroxy-xanthene

Also Published As

Publication number Publication date
BE600735A (en) 1961-08-28
DE1210890B (en) 1966-02-17
FR1002M (en) 1961-12-18
GB925538A (en) 1963-05-08
SE333573B (en) 1971-03-22
DE1518325B1 (en) 1970-08-27

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