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
- LPJDUOFFJNDMLP-UHFFFAOYSA-N 2-(trifluoromethyl)thiopyrano[3,2-b]chromene Chemical compound FC(F)(F)C=1SC2=CC3=CC=CC=C3OC2=CC1 LPJDUOFFJNDMLP-UHFFFAOYSA-N 0.000 title 1
- -1 trifluoromethyl xanthenes Chemical class 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- GMPKQJAYGPIGIX-UHFFFAOYSA-N 1-(2-phenylmethoxyethyl)piperazine Chemical compound C=1C=CC=CC=1COCCN1CCNCC1 GMPKQJAYGPIGIX-UHFFFAOYSA-N 0.000 abstract 1
- LUWMSPXXRXPGEX-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(1-phenylmethoxyethyl)piperazine Chemical compound C(C1=CC=CC=C1)OC(C)N1CCN(CC1)CCCCl LUWMSPXXRXPGEX-UHFFFAOYSA-N 0.000 abstract 1
- RCYYTODXXGVYOM-UHFFFAOYSA-N 1-(trifluoromethyl)xanthen-9-one Chemical compound FC(C1=CC=CC=2OC3=CC=CC=C3C(C12)=O)(F)F RCYYTODXXGVYOM-UHFFFAOYSA-N 0.000 abstract 1
- RECMXJOGNNTEBG-UHFFFAOYSA-N 1-phenylmethoxyethanol Chemical compound CC(O)OCC1=CC=CC=C1 RECMXJOGNNTEBG-UHFFFAOYSA-N 0.000 abstract 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 abstract 1
- KAVWAZMQANHFGV-UHFFFAOYSA-N 3-[4-(1-phenylmethoxyethyl)piperazin-1-yl]propan-1-ol Chemical compound C(C1=CC=CC=C1)OC(C)N1CCN(CC1)CCCO KAVWAZMQANHFGV-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- QYPQNGCEVAYREM-UHFFFAOYSA-N ethyl 4-(1-phenylmethoxyethyl)piperazine-1-carboxylate Chemical compound C(C1=CC=CC=C1)OC(C)N1CCN(CC1)C(=O)OCC QYPQNGCEVAYREM-UHFFFAOYSA-N 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 abstract 1
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)
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 (enExample) |
| DE (2) | DE1210890B (enExample) |
| FR (1) | FR1002M (enExample) |
| GB (2) | GB925538A (enExample) |
| SE (1) | SE333573B (enExample) |
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 (zh) * | 2015-03-09 | 2015-06-10 | 广东帅广医药有限公司 | 一种盐酸氟哌噻吨的制备方法 |
| CN107987053A (zh) * | 2017-12-08 | 2018-05-04 | 重庆植恩药业有限公司 | 一种高纯度z型盐酸氟哌噻吨的制备方法 |
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 (de) * | 1956-06-12 | 1958-11-20 | Hoffmann La Roche | Verfahren zur Herstellung von Xanthen- bzw. Thioxanthenderivaten |
| AT202143B (de) * | 1956-12-28 | 1959-02-10 | American Cyanamid Co | Verfahren zur Herstellung von neuen Dimethylaminopropylidenxanthenen |
| AT202152B (de) * | 1956-12-28 | 1959-02-10 | American Cyanamid Co | Verfahren zur Herstellung von neuen Dimethylaminopropylidenthiaxanthenen. |
| FR1173489A (fr) * | 1957-04-04 | 1959-02-25 | Merck & Co Inc | Thiaxanthènes substitués |
-
1961
- 1961-02-14 DE DES72528A patent/DE1210890B/de active Pending
- 1961-02-14 DE DE19611518325 patent/DE1518325B1/de active Pending
- 1961-02-28 FR FR854116A patent/FR1002M/fr active Active
- 1961-02-28 BE BE600735A patent/BE600735A/fr unknown
- 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 (zh) * | 2015-03-09 | 2015-06-10 | 广东帅广医药有限公司 | 一种盐酸氟哌噻吨的制备方法 |
| CN107987053A (zh) * | 2017-12-08 | 2018-05-04 | 重庆植恩药业有限公司 | 一种高纯度z型盐酸氟哌噻吨的制备方法 |
| CN107987053B (zh) * | 2017-12-08 | 2023-04-14 | 植恩生物技术股份有限公司 | 一种高纯度z型盐酸氟哌噻吨的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1002M (fr) | 1961-12-18 |
| BE600735A (fr) | 1961-08-28 |
| DE1518325B1 (de) | 1970-08-27 |
| GB925539A (en) | 1963-05-08 |
| DE1210890B (de) | 1966-02-17 |
| SE333573B (enExample) | 1971-03-22 |
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