IE38554L - Piperazinyl-thiaxanthenes. - Google Patents
Piperazinyl-thiaxanthenes.Info
- Publication number
- IE38554L IE38554L IE732161A IE216173A IE38554L IE 38554 L IE38554 L IE 38554L IE 732161 A IE732161 A IE 732161A IE 216173 A IE216173 A IE 216173A IE 38554 L IE38554 L IE 38554L
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- nme
- reacting
- fluorothiaxanth
- ylidene
- Prior art date
Links
- -1 Piperazinyl-thiaxanthenes Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 2
- 101150065749 Churc1 gene Proteins 0.000 abstract 2
- 102100038239 Protein Churchill Human genes 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- LFJMRGTVKNCAKR-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(2-methoxyethyl)piperazine Chemical compound COCCN1CCN(CCCCl)CC1 LFJMRGTVKNCAKR-UHFFFAOYSA-N 0.000 abstract 1
- CIBQTAHLHLHRGX-UHFFFAOYSA-N 3-fluoro-9H-thioxanthene Chemical class FC=1C=CC=2CC3=CC=CC=C3SC=2C=1 CIBQTAHLHLHRGX-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1453828 Thiaxanthene derivatives KEFALAS AS 28 Nov 1973 [8 Dec 1972] 56910/72 Heading C2C The invention comprises compounds of formula and their addition salts with pharmaceutically acceptable acids, wherein X is Cl, CF 3 or SO 2 NMe 2 ; Z is >CHCH 2 - or >C : CH-; and Y is >NH, >NMe, >NCH 2 CH 2 OH or > CHCH 2 CH 2 OH, and the esters of these alcohols with C 1-17 alkanoic acids. In examples, these compounds are prepared by (1) reducing the unsaturated to the saturated compounds; (2) reacting the analogues having the side-chain terminated by: CH 2 , Cl or NMe 2 with (3) forming the compound where Y is by reacting that where Y is >NH with ethylene oxide; (4) esterifying the alcohols; (5) reacting a 9-Li derivative of a 9-unsubstituted 3-fluorothioxanthene (which is derived from the corresponding thiaxanthone) with (6) splitting the corresponding methyl ether of the desired alcohol. Analogues of the compounds (I) having a 5- or 6-Cl or CF 3 substituent instead of 6-F are also disclosed. Starting materials and intermediates otherwise described are 1-(3-chloropropyl)-4-(2-methoxyethyl)piperazine, and those of formulµ R<SP>2</SP>(-OH)CH 2 CH : CH 2 and R<SP>2</SP> : O, where R is 3-FC 6 H 4 , R<SP>1</SP> is 2-chloro(or trifluoromethyl)-6- fluorothiaxanth-9-ylidene, and R<SP>2</SP> is 2-dimethylsulphamoyl-6-fluorothiaxanth-9-ylidene. Therapeutic compositions having neuroleptic activity comprise compounds of the above formula, and may be administered orally or parenterally.
[GB1453828A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5691072A GB1453828A (en) | 1972-12-08 | 1972-12-08 | Fluoro-substituted thiaxanthene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38554L true IE38554L (en) | 1974-06-08 |
| IE38554B1 IE38554B1 (en) | 1978-04-12 |
Family
ID=10477876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2161/73A IE38554B1 (en) | 1972-12-08 | 1973-11-29 | Fluoro-substituted thiaxanthene derivatives |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS594436B2 (en) |
| AR (2) | AR202805A1 (en) |
| AT (1) | AT332395B (en) |
| BE (1) | BE808347A (en) |
| CH (2) | CH592085A5 (en) |
| CS (1) | CS176259B2 (en) |
| DE (1) | DE2359359C3 (en) |
| DK (1) | DK145576C (en) |
| ES (2) | ES421098A1 (en) |
| FI (1) | FI57410C (en) |
| FR (1) | FR2209573B1 (en) |
| GB (1) | GB1453828A (en) |
| HU (1) | HU167778B (en) |
| IE (1) | IE38554B1 (en) |
| NL (1) | NL7316035A (en) |
| NO (1) | NO138806C (en) |
| PL (1) | PL95266B1 (en) |
| SE (1) | SE400287B (en) |
| ZA (1) | ZA738990B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ189108A (en) * | 1977-12-29 | 1982-02-23 | Kefalas As | 2-methylthio-6-fluoro-9-(1-methyl-4-piperidylidene)-thioxanthene and pharmaceutical compositions intermediate 2-methylthio-6-fluoro-9-(1-methyl-4-piperidyl)-thioxanthen-9-ol |
| US5173489A (en) * | 1986-04-10 | 1992-12-22 | The Dupont Merck Pharmaceutical Co. | α,α-disubstituted aromatics and heteroaromatics as cognition enhancers |
| GB8628903D0 (en) * | 1986-12-03 | 1987-01-07 | Lunbeck A S H | Neuroleptic compounds |
| US6395752B1 (en) * | 1999-03-04 | 2002-05-28 | Pharmaquest Limited | Method of treating depression using 1-threo-methylphenidate |
| US6127385A (en) * | 1999-03-04 | 2000-10-03 | Pharmaquest Limited | Method of treating depression using l-threo-methylphenidate |
| WO2008080398A1 (en) * | 2007-01-05 | 2008-07-10 | Bkg Pharma Aps | Anti - infective agents such as phenothiazine and thioxanthene derivates to treat infectious diseases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE585338A (en) * | 1958-12-04 | |||
| FR1463787A (en) * | 1963-10-14 | 1966-07-22 | Pfizer & Co C | Aminoalkyl-trisubstituted phosphonium compounds, derivatives of such compounds, and processes for their preparation |
-
1972
- 1972-12-08 GB GB5691072A patent/GB1453828A/en not_active Expired
-
1973
- 1973-11-23 FI FI3618/73A patent/FI57410C/en active
- 1973-11-23 CH CH1585676A patent/CH592085A5/xx not_active IP Right Cessation
- 1973-11-23 NL NL7316035A patent/NL7316035A/xx not_active Application Discontinuation
- 1973-11-23 CH CH1652873A patent/CH590272A5/xx not_active IP Right Cessation
- 1973-11-26 ZA ZA738990A patent/ZA738990B/en unknown
- 1973-11-28 DE DE2359359A patent/DE2359359C3/en not_active Expired
- 1973-11-29 AT AT1000373A patent/AT332395B/en not_active IP Right Cessation
- 1973-11-29 IE IE2161/73A patent/IE38554B1/en unknown
- 1973-12-03 ES ES421098A patent/ES421098A1/en not_active Expired
- 1973-12-06 CS CS8429A patent/CS176259B2/cs unknown
- 1973-12-07 NO NO4693/73A patent/NO138806C/en unknown
- 1973-12-07 JP JP48136256A patent/JPS594436B2/en not_active Expired
- 1973-12-07 SE SE7316567A patent/SE400287B/en unknown
- 1973-12-07 AR AR251406A patent/AR202805A1/en active
- 1973-12-07 HU HUKE936A patent/HU167778B/hu unknown
- 1973-12-07 FR FR7343766A patent/FR2209573B1/fr not_active Expired
- 1973-12-07 BE BE138618A patent/BE808347A/en not_active IP Right Cessation
- 1973-12-07 PL PL1973178366A patent/PL95266B1/en unknown
- 1973-12-10 DK DK667273A patent/DK145576C/en active
-
1974
- 1974-11-19 AR AR256579A patent/AR202672A1/en active
-
1976
- 1976-01-14 ES ES444294A patent/ES444294A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO138806B (en) | 1978-08-07 |
| GB1453828A (en) | 1976-10-27 |
| AR202805A1 (en) | 1975-07-24 |
| JPS594436B2 (en) | 1984-01-30 |
| AT332395B (en) | 1976-09-27 |
| AR202672A1 (en) | 1975-06-30 |
| ATA1000373A (en) | 1976-01-15 |
| SE400287B (en) | 1978-03-20 |
| CH590272A5 (en) | 1977-07-29 |
| ZA738990B (en) | 1974-11-27 |
| HU167778B (en) | 1975-12-25 |
| DE2359359C3 (en) | 1978-11-02 |
| IE38554B1 (en) | 1978-04-12 |
| FI57410C (en) | 1980-08-11 |
| FR2209573B1 (en) | 1977-12-09 |
| NL7316035A (en) | 1974-06-11 |
| DE2359359B2 (en) | 1978-02-16 |
| DE2359359A1 (en) | 1974-06-27 |
| PL95266B1 (en) | 1977-10-31 |
| NO138806C (en) | 1978-11-15 |
| CH592085A5 (en) | 1977-10-14 |
| FI57410B (en) | 1980-04-30 |
| ES444294A1 (en) | 1977-10-01 |
| JPS4994691A (en) | 1974-09-09 |
| AU6296673A (en) | 1975-05-29 |
| ES421098A1 (en) | 1976-08-01 |
| BE808347A (en) | 1974-03-29 |
| CS176259B2 (en) | 1977-06-30 |
| DK145576B (en) | 1982-12-13 |
| FR2209573A1 (en) | 1974-07-05 |
| DK145576C (en) | 1983-06-13 |
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