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GB1453828A - Fluoro-substituted thiaxanthene derivatives - Google Patents

Fluoro-substituted thiaxanthene derivatives

Info

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
Application number
GB5691072A
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.)
H Lundbeck AS
Original Assignee
Kefalas AS
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
Application filed by Kefalas AS filed Critical Kefalas AS
Priority to GB5691072A priority Critical patent/GB1453828A/en
Priority to NL7316035A priority patent/NL7316035A/xx
Priority to CH1585676A priority patent/CH592085A5/xx
Priority to CH1652873A priority patent/CH590272A5/xx
Priority to FI3618/73A priority patent/FI57410C/en
Priority to ZA738990A priority patent/ZA738990B/en
Priority to DE2359359A priority patent/DE2359359C3/en
Priority to AU62966/73A priority patent/AU477427B2/en
Priority to AT1000373A priority patent/AT332395B/en
Priority to IE2161/73A priority patent/IE38554B1/en
Priority to ES421098A priority patent/ES421098A1/en
Priority to CS8429A priority patent/CS176259B2/cs
Priority to FR7343766A priority patent/FR2209573B1/fr
Priority to PL1973178366A priority patent/PL95266B1/en
Priority to AR251406A priority patent/AR202805A1/en
Priority to JP48136256A priority patent/JPS594436B2/en
Priority to HUKE936A priority patent/HU167778B/hu
Priority to NO4693/73A priority patent/NO138806C/en
Priority to BE138618A priority patent/BE808347A/en
Priority to SE7316567A priority patent/SE400287B/en
Priority to CA187,713A priority patent/CA1010870A/en
Priority to DK667273A priority patent/DK145576C/en
Priority to AR256579A priority patent/AR202672A1/en
Priority to US05/593,559 priority patent/US4044024A/en
Priority to US05/604,462 priority patent/US4042695A/en
Priority to ES444294A priority patent/ES444294A1/en
Publication of GB1453828A publication Critical patent/GB1453828A/en
Expired legal-status Critical Current

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)
  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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.
GB5691072A 1972-12-08 1972-12-08 Fluoro-substituted thiaxanthene derivatives Expired GB1453828A (en)

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
CH1585676A CH592085A5 (en) 1972-12-08 1973-11-23
CH1652873A CH590272A5 (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
ZA738990A ZA738990B (en) 1972-12-08 1973-11-26 Heterocyclic organic compounds
DE2359359A DE2359359C3 (en) 1972-12-08 1973-11-28 Fluorine-substituted thioxanthenes, processes for their preparation and neuroleptic agents containing them
AU62966/73A AU477427B2 (en) 1972-12-08 1973-11-28 2-fluoro-substituted thiazanthene derivatives
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
FR7343766A FR2209573B1 (en) 1972-12-08 1973-12-07
PL1973178366A PL95266B1 (en) 1972-12-08 1973-12-07 METHOD OF PRODUCTION OF NEW DERIVATIVES OF THIAXANTHENE
AR251406A AR202805A1 (en) 1972-12-08 1973-12-07 METHOD FOR THE PREPARATION OF THIAXANTHENES, FLUOR-SUBSTITUTES
JP48136256A JPS594436B2 (en) 1972-12-08 1973-12-07 Manufacturing method of heterocyclic compounds
HUKE936A HU167778B (en) 1972-12-08 1973-12-07
NO4693/73A NO138806C (en) 1972-12-08 1973-12-07 ANALOGICAL PROCEDURE FOR PREPARING NEUROLEPTIC ACTIVE 6-FLUOR-SUBSTITUTED THIAXANTENE DERIVATIVES
BE138618A BE808347A (en) 1972-12-08 1973-12-07 HETEROCYCLIC COMPOUNDS AND METHOD OF PREPARATION OF THEM
SE7316567A SE400287B (en) 1972-12-08 1973-12-07 PROCEDURE FOR THE PREPARATION OF FLUORO-SUBSTITUTED THIAXANTENE DERIVATIVES
CA187,713A CA1010870A (en) 1972-12-08 1973-12-07 Thiaxanthene derivative and method
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) CH590272A5 (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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (6)

* Cited by examiner, † Cited by third party
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
HU167778B (en) 1975-12-25
CH592085A5 (en) 1977-10-14
DE2359359A1 (en) 1974-06-27
AR202805A1 (en) 1975-07-24
ES421098A1 (en) 1976-08-01
BE808347A (en) 1974-03-29
FI57410B (en) 1980-04-30
AU6296673A (en) 1975-05-29
FR2209573A1 (en) 1974-07-05
JPS4994691A (en) 1974-09-09
CS176259B2 (en) 1977-06-30
DE2359359B2 (en) 1978-02-16
NL7316035A (en) 1974-06-11
DK145576C (en) 1983-06-13
PL95266B1 (en) 1977-10-31
ZA738990B (en) 1974-11-27
FI57410C (en) 1980-08-11
AR202672A1 (en) 1975-06-30
NO138806C (en) 1978-11-15
CH590272A5 (en) 1977-07-29
FR2209573B1 (en) 1977-12-09
AT332395B (en) 1976-09-27
NO138806B (en) 1978-08-07
DK145576B (en) 1982-12-13
SE400287B (en) 1978-03-20
JPS594436B2 (en) 1984-01-30
IE38554B1 (en) 1978-04-12
ES444294A1 (en) 1977-10-01
IE38554L (en) 1974-06-08
ATA1000373A (en) 1976-01-15
DE2359359C3 (en) 1978-11-02

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee