GB925538A - Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivatives - Google Patents
Improvements in or relating to trifluoromethylthiaxanthene and -xanthene derivativesInfo
- Publication number
- GB925538A GB925538A GB793161A GB793161A GB925538A GB 925538 A GB925538 A GB 925538A GB 793161 A GB793161 A GB 793161A GB 793161 A GB793161 A GB 793161A GB 925538 A GB925538 A GB 925538A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- give
- benzyloxyethyl
- piperazine
- aminoalkyl
- 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
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 trifluoromethyl xanthenes and thiaxanthenes of the formula <FORM:0925538/IV(a)/1> and their salts, wherein Y = S or O, R1 = H or OH when R2 is hydrogen, R1 and R2 taken together form a single bond, R3 = H or CH3 and Z is a basic nitrogen containing radical of not more than 15 carbon atoms such as dialkylamino, pyrrolidino, piperidino and 4-alkyl-, hydroxyalkyl-, acetoxyalkyl-, carbamoyloxyalkyl-, dialkylcarbamoyloxyalkyl-, hydroxyethoxyethyl-, hydroxyethoxyethoxyethyl- and benzoyloxyalkyl-substituted piperazino groups. The trifluoromethyl group is preferably in the 2-position of the xanthene or thiaxanthene ring. The compounds are made by reacting a trifluoromethylxanthenone or thiaxanthenone with an aminoalkyl magnesium halide Z,CH2,CH(R3),CH2,Mg.Halogen, dehydrating the resulting 10-aminoalkyl-10- hydroxytrifluoromethylxanthene or thiaxanthene by treatment with acid such as hydrochloric or sulphuric acid, or with an acid anhydride such as acetic anhydride to give the corresponding aminoalkylidene compounds of the invention, and, if desired, reducing, e.g. by catalytic hydrogenation to give the aminoalkyl compounds. Benzyloxyalkylpiperazinyl compounds prepared by the above procedures may be treated with mineral acid to give a hydroxyalkylpiperazinyl derivative which may in turn be acylated to give the corresponding acetoxyalkyl and dialkylcarbamoyloxyalkyl compounds or may be chlorinated to give a chloroalkylpiperazinyl compound, e.g. a chloroethylpiperazinyl compound from which hydroxyethoxyethyl or hydroxyethoxyethoxyethyl compounds are made by treatment with an appropriate glycol. The carbamoyloxalkyl-piperazino compounds are made by converting the hydroxyalkyl piperazino compounds to the phenyl carbonate salt and treating with ammonia. The products are used pharmaceutically suitably in the form of their salts with organic and inorganic acids (many specified). 1-Benzyloxyethyl- 4-chloropropylpiperazine is made by converting benzyloxyethanol into its p-toluenesulphonate, reacting with N-ethoxycarbonyl-piperazine to give 1-benzyloxyethyl-4-ethoxycarbonyl-piperazine, hydrolysing and decarboxylating to N-benzyloxyethylpiperazine, reacting with 3-bromopropanol to give 1-benzyloxyethyl-4-(3-hydroxypropyl)-piperazine and chlorinating with thionyl chloride. Specification 925,539 is referred to.
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 |
|---|---|
| GB925538A true GB925538A (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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1914062A Expired GB925539A (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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157658A (en) * | 1963-07-05 | 1964-11-17 | Searle & Co | 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds |
| US3159636A (en) * | 1963-07-05 | 1964-12-01 | Searle & Co | 1-amino-4-(xanthenyl and thioxanthenyl) piperazines |
| US5104858A (en) * | 1988-09-29 | 1992-04-14 | Yale University | Sensitizing multidrug resistant cells to antitumor agents |
| WO2005037820A1 (en) * | 2003-10-17 | 2005-04-28 | Laboratorio Chimico Internazionale S.P.A. | Process for the preparation of z-flupentixol |
| WO2005105145A1 (en) | 2004-04-30 | 2005-11-10 | Bkg Pharma Aps | Treatment of infectious diseases |
| EP2301545A1 (en) | 2007-01-05 | 2011-03-30 | BKG Pharma ApS | Thioxanthene derivatives for use in the treatment of infectious diseases |
| EP2374450A1 (en) | 2010-04-06 | 2011-10-12 | H. Lundbeck A/S | Flupentixol compositions |
| CN104693173A (en) * | 2015-03-09 | 2015-06-10 | 广东帅广医药有限公司 | Preparation method of flupentixol hydrochloride |
| CN107987053A (en) * | 2017-12-08 | 2018-05-04 | 重庆植恩药业有限公司 | A kind of preparation method of high-purity Z-type Flupenthixol Hydrochloride |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5196549A (en) * | 1991-06-11 | 1993-03-23 | 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-xanthane |
Family Cites Families (4)
| 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 |
-
1961
- 1961-02-14 DE DES72528A patent/DE1210890B/en active Pending
- 1961-02-14 DE DE19611518325 patent/DE1518325B1/en active Pending
- 1961-02-28 BE BE600735A patent/BE600735A/en unknown
- 1961-02-28 FR FR854116A patent/FR1002M/en active Active
- 1961-03-03 GB GB793161A patent/GB925538A/en not_active Expired
- 1961-03-03 GB GB1914062A patent/GB925539A/en not_active Expired
-
1965
- 1965-08-23 SE SE11002/65A patent/SE333573B/xx unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157658A (en) * | 1963-07-05 | 1964-11-17 | Searle & Co | 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds |
| US3159636A (en) * | 1963-07-05 | 1964-12-01 | Searle & Co | 1-amino-4-(xanthenyl and thioxanthenyl) piperazines |
| US5104858A (en) * | 1988-09-29 | 1992-04-14 | Yale University | Sensitizing multidrug resistant cells to antitumor agents |
| WO2005037820A1 (en) * | 2003-10-17 | 2005-04-28 | Laboratorio Chimico Internazionale S.P.A. | Process for the preparation of z-flupentixol |
| WO2005105145A1 (en) | 2004-04-30 | 2005-11-10 | Bkg Pharma Aps | Treatment of infectious diseases |
| EP2260870A2 (en) | 2004-04-30 | 2010-12-15 | BKG Pharma ApS | Treatment of infectious diseases with combinations of a thioxanthene derivative with an anti-infective agent |
| EP2301545A1 (en) | 2007-01-05 | 2011-03-30 | BKG Pharma ApS | Thioxanthene derivatives for use in the treatment of infectious diseases |
| EP2374450A1 (en) | 2010-04-06 | 2011-10-12 | H. Lundbeck A/S | Flupentixol compositions |
| CN104693173A (en) * | 2015-03-09 | 2015-06-10 | 广东帅广医药有限公司 | Preparation method of flupentixol hydrochloride |
| CN107987053A (en) * | 2017-12-08 | 2018-05-04 | 重庆植恩药业有限公司 | A kind of preparation method of high-purity Z-type Flupenthixol 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE600735A (en) | 1961-08-28 |
| DE1210890B (en) | 1966-02-17 |
| FR1002M (en) | 1961-12-18 |
| SE333573B (en) | 1971-03-22 |
| GB925539A (en) | 1963-05-08 |
| DE1518325B1 (en) | 1970-08-27 |
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