GB1453828A - Fluoro-substituted thiaxanthene derivatives - Google Patents
Fluoro-substituted thiaxanthene derivativesInfo
- Publication number
- GB1453828A GB1453828A GB5691072A GB5691072A GB1453828A GB 1453828 A GB1453828 A GB 1453828A GB 5691072 A GB5691072 A GB 5691072A GB 5691072 A GB5691072 A GB 5691072A GB 1453828 A GB1453828 A GB 1453828A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- nme
- reacting
- fluorothiaxanth
- ylidene
- 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
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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.
Priority Applications (26)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5691072A GB1453828A (en) | 1972-12-08 | 1972-12-08 | Fluoro-substituted thiaxanthene derivatives |
NL7316035A NL7316035A (en) | 1972-12-08 | 1973-11-23 | |
FI3618/73A FI57410C (en) | 1972-12-08 | 1973-11-23 | FREQUENCY REFRIGERATION OF NEW NEUROLEPTISTS ACTIVE 6-FLUORINE SUBSTITUTES WITHOUT DESSAS SALTER |
CH1585676A CH592085A5 (en) | 1972-12-08 | 1973-11-23 | |
CH1652873A CH590272A5 (en) | 1972-12-08 | 1973-11-23 | |
ZA738990A ZA738990B (en) | 1972-12-08 | 1973-11-26 | Heterocyclic organic compounds |
AU62966/73A AU477427B2 (en) | 1972-12-08 | 1973-11-28 | 2-fluoro-substituted thiazanthene derivatives |
DE2359359A DE2359359C3 (en) | 1972-12-08 | 1973-11-28 | Fluorine-substituted thioxanthenes, processes for their preparation and neuroleptic agents containing them |
AT1000373A AT332395B (en) | 1972-12-08 | 1973-11-29 | PROCESS FOR THE PRODUCTION OF NEW FLUORINE SUBSTITUTED THIOXANTHENS |
IE2161/73A IE38554B1 (en) | 1972-12-08 | 1973-11-29 | Fluoro-substituted thiaxanthene derivatives |
ES421098A ES421098A1 (en) | 1972-12-08 | 1973-12-03 | Fluoro-substituted thiaxanthene derivatives |
CS8429A CS176259B2 (en) | 1972-12-08 | 1973-12-06 | |
AR251406A AR202805A1 (en) | 1972-12-08 | 1973-12-07 | METHOD FOR THE PREPARATION OF THIAXANTHENES, FLUOR-SUBSTITUTES |
BE138618A BE808347A (en) | 1972-12-08 | 1973-12-07 | HETEROCYCLIC COMPOUNDS AND METHOD OF PREPARATION OF THEM |
CA187,713A CA1010870A (en) | 1972-12-08 | 1973-12-07 | Thiaxanthene derivative and method |
PL1973178366A PL95266B1 (en) | 1972-12-08 | 1973-12-07 | METHOD OF PRODUCTION OF NEW DERIVATIVES OF THIAXANTHENE |
FR7343766A FR2209573B1 (en) | 1972-12-08 | 1973-12-07 | |
SE7316567A SE400287B (en) | 1972-12-08 | 1973-12-07 | PROCEDURE FOR THE PREPARATION OF FLUORO-SUBSTITUTED THIAXANTENE DERIVATIVES |
NO4693/73A NO138806C (en) | 1972-12-08 | 1973-12-07 | ANALOGICAL PROCEDURE FOR PREPARING NEUROLEPTIC ACTIVE 6-FLUOR-SUBSTITUTED THIAXANTENE DERIVATIVES |
JP48136256A JPS594436B2 (en) | 1972-12-08 | 1973-12-07 | Manufacturing method of heterocyclic compounds |
HUKE936A HU167778B (en) | 1972-12-08 | 1973-12-07 | |
DK667273A DK145576C (en) | 1972-12-08 | 1973-12-10 | METHOD OF ANALOGUE FOR THE PREPARATION OF 6-FLUORO-SUBSTITUTED THIOXANTHENES OR ACID ADDITION SALTS. |
AR256579A AR202672A1 (en) | 1972-12-08 | 1974-11-19 | METHOD FOR THE PREPARATION OF FLUORSUSTITUTED THIAXANTHENS |
US05/593,559 US4044024A (en) | 1972-12-08 | 1975-07-07 | Thiaxanthene derivatives |
US05/604,462 US4042695A (en) | 1972-12-08 | 1975-08-13 | Thiaxanthene derivatives, compositions thereof and methods of treating therewith |
ES444294A ES444294A1 (en) | 1972-12-08 | 1976-01-14 | Fluoro-substituted thiaxanthene derivatives |
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 (1)
Publication Number | Publication Date |
---|---|
GB1453828A true GB1453828A (en) | 1976-10-27 |
Family
ID=10477876
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5691072A Expired GB1453828A (en) | 1972-12-08 | 1972-12-08 | 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) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002902A1 (en) * | 1977-12-29 | 1979-07-11 | Kefalas A/S | Methylthiofluorothioxanthene derivative, its preparation and compositions containing it |
US6127385A (en) * | 1999-03-04 | 2000-10-03 | Pharmaquest Limited | Method of treating depression using l-threo-methylphenidate |
US6395752B1 (en) * | 1999-03-04 | 2002-05-28 | Pharmaquest Limited | Method of treating depression using 1-threo-methylphenidate |
EP2301545A1 (en) * | 2007-01-05 | 2011-03-30 | BKG Pharma ApS | Thioxanthene derivatives for use in the treatment of infectious diseases |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 NL NL7316035A patent/NL7316035A/xx not_active Application Discontinuation
- 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 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 IE IE2161/73A patent/IE38554B1/en unknown
- 1973-11-29 AT AT1000373A patent/AT332395B/en not_active IP Right Cessation
- 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 FR FR7343766A patent/FR2209573B1/fr not_active Expired
- 1973-12-07 BE BE138618A patent/BE808347A/en not_active IP Right Cessation
- 1973-12-07 SE SE7316567A patent/SE400287B/en unknown
- 1973-12-07 PL PL1973178366A patent/PL95266B1/en unknown
- 1973-12-07 HU HUKE936A patent/HU167778B/hu unknown
- 1973-12-07 AR AR251406A patent/AR202805A1/en active
- 1973-12-07 JP JP48136256A patent/JPS594436B2/en not_active Expired
- 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
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002902A1 (en) * | 1977-12-29 | 1979-07-11 | Kefalas A/S | Methylthiofluorothioxanthene derivative, its preparation and compositions containing it |
US4235916A (en) * | 1977-12-29 | 1980-11-25 | Kefalas A/S | 2-Methylthio-6-fluoro-9-(1-methyl-4-piperidylidene)-thioxanthene and salts thereof, neuroleptic compositions and method of use |
US6127385A (en) * | 1999-03-04 | 2000-10-03 | Pharmaquest Limited | Method of treating depression using l-threo-methylphenidate |
US6395752B1 (en) * | 1999-03-04 | 2002-05-28 | Pharmaquest Limited | Method of treating depression using 1-threo-methylphenidate |
EP2301545A1 (en) * | 2007-01-05 | 2011-03-30 | BKG Pharma ApS | Thioxanthene derivatives for use in the treatment of infectious diseases |
AU2008203743B2 (en) * | 2007-01-05 | 2012-07-12 | Bkg Pharma Aps | Thioxanthene derivates useful to treat infectious diseases |
Also Published As
Publication number | Publication date |
---|---|
FI57410C (en) | 1980-08-11 |
BE808347A (en) | 1974-03-29 |
DE2359359C3 (en) | 1978-11-02 |
JPS4994691A (en) | 1974-09-09 |
NL7316035A (en) | 1974-06-11 |
NO138806B (en) | 1978-08-07 |
NO138806C (en) | 1978-11-15 |
IE38554L (en) | 1974-06-08 |
IE38554B1 (en) | 1978-04-12 |
HU167778B (en) | 1975-12-25 |
ATA1000373A (en) | 1976-01-15 |
AT332395B (en) | 1976-09-27 |
AR202672A1 (en) | 1975-06-30 |
FI57410B (en) | 1980-04-30 |
CH590272A5 (en) | 1977-07-29 |
FR2209573B1 (en) | 1977-12-09 |
AR202805A1 (en) | 1975-07-24 |
CS176259B2 (en) | 1977-06-30 |
DE2359359B2 (en) | 1978-02-16 |
JPS594436B2 (en) | 1984-01-30 |
CH592085A5 (en) | 1977-10-14 |
SE400287B (en) | 1978-03-20 |
PL95266B1 (en) | 1977-10-31 |
ES421098A1 (en) | 1976-08-01 |
ZA738990B (en) | 1974-11-27 |
AU6296673A (en) | 1975-05-29 |
DE2359359A1 (en) | 1974-06-27 |
DK145576C (en) | 1983-06-13 |
DK145576B (en) | 1982-12-13 |
ES444294A1 (en) | 1977-10-01 |
FR2209573A1 (en) | 1974-07-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR870007119A (en) | Quinone derivatives, their preparation and uses | |
IE34511B1 (en) | Heterocyclic ethers of-1-substituted-4-hydroxyalkyl piperazines and process for preparing them | |
GB1453828A (en) | Fluoro-substituted thiaxanthene derivatives | |
GB1155936A (en) | Novel Sulphonamides and a Process for the Manufacture thereof | |
SE7608037L (en) | 2-SUBSTITUTED OXAZOLOPYRIDINES | |
GB1289240A (en) | ||
GB1515060A (en) | 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters | |
GB1495665A (en) | Pyrimidines | |
ES8105254A1 (en) | Alkanoic acid derivatives | |
SE8204393D0 (en) | NEW BICYCLIC COMPOUNDS AND A PROCESS FOR THE PREPARATION THEREOF | |
GB1298432A (en) | Phenyl-azolyl-fatty acid derivatives, process for their production and their use as medicines | |
RU95107150A (en) | Derivatives of pyridobenzoxadiazine carboxylic acid mixture of their isomers or individual isomers, their pharmaceutically acceptable hydrates and salts, intermediate products for their production, and pharmaceutical composition having antibactericidal activity on their base | |
IL44837A (en) | Sulfur containing trialkoxybenzoylamino-carboxylic acids their preparation and pharmaceutical compositions containing them | |
GB1377306A (en) | Esters of 2-quinoxalinecarboxylic acid di n-oxide | |
ES278797A1 (en) | New uracil derivatives and process for their production | |
GB1073485A (en) | New 1-subustituted cycloheptimidaszol-2(1h)-one compounds and a process for the same | |
IE33364L (en) | Morpholino- and thiomorpholino-pyrimidines. | |
GB1510423A (en) | Oxadiazole derivatives and their salts process for their preparation and compositions incorporating them | |
GB1079989A (en) | Carbocyclic propanolamines | |
GB1425808A (en) | Pharmaceutically useful prostanoic acid derivatives | |
GB1390250A (en) | Indole fused heterocyclic compounds | |
ES266759A1 (en) | 1-[nu-lower alkyl-piperidyl-(4')]-3-phenyl-4-(parasubstituted benzyl)-pyrazolones | |
GB1366319A (en) | Sa 8-amino-theohylline derivatives process for their preparation and therapeutic compositon containing same | |
GB1140471A (en) | Phenthiazine derivatives | |
IT1210604B (en) | 2-Oxo-alkyl sulphonate ester(s) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |