GB1409898A - 1,1-dioxidothiazolidin-4-ones and processes for their manufacture - Google Patents

1,1-dioxidothiazolidin-4-ones and processes for their manufacture

Info

Publication number
GB1409898A
GB1409898A GB5603172A GB5603172A GB1409898A GB 1409898 A GB1409898 A GB 1409898A GB 5603172 A GB5603172 A GB 5603172A GB 5603172 A GB5603172 A GB 5603172A GB 1409898 A GB1409898 A GB 1409898A
Authority
GB
United Kingdom
Prior art keywords
halogen atom
atom
dioxido
thiazolidin
ones
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
GB5603172A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1409898A publication Critical patent/GB1409898A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
    • C07D277/14—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

1409898 1,1-Dioxido-5-halo-thiazolidin-4- ones CIBA-GEIGY AG 5 Dec 1972 [6 Dec 1971] 56031/72 Heading C2C Novel 1,1 -dioxido-5-halo-thiazolidin-4-ones of the general formula wherein each of R 1 and R 2 is a hydrogen atom, an aliphatic, araliphatic or aryl group or a 5-membered heterocyclic group containing O and/or S atoms, or R 1 and R 2 , together with the carbon atom to which they are attached, form a cycloaliphatic ring of 5-8 C atoms, R 3 is an aliphatic, cycloaliphatic, araliphatic or aryl group or a heterocyclic group which is bonded to the ring nitrogen atom directly or via 1-3 methylene groups, and each of R 4 and R 5 is a halogen atom or R 4 is a hydrogen atom or a C 1-5 alkyl or aryl group and R 5 is a halogen atom, are prepared (a) by reacting compounds of the general formulae and wherein Y is a chlorine or bromine atom, in the presence of liquid SO 2 and a tertiary organic base; and (b) when R 4 is a hydrogen atom and R 5 is a halogen atom, by reducing the corresponding compound in which R 4 is a halogen atom. 1,1-Dioxido-thiazolidin-4-ones (A) of the first general formula above wherein each of R 4 and R 5 is a hydrogen atom are prepared by reducing the corresponding compound in which R 4 is a hydrogen or halogen atom and R 5 is a halogen atom. 1,1-Dioxido-thiazolidin-4-ones (B) of the first general formula above wherein R 4 is a C 1-5 alkyl or aryl group and R 5 is a hydrogen atom are prepared by reducing the corresponding compound in which R 5 is a halogen atom. 1,4 - Diphenyl - 3 - n - butyl - 3 - chloroazetidin-2-one is obtained as a by-product in process (a) above. N - (2<SP>1</SP>,6<SP>1</SP> - Dichlorobenzylidene)- isopropylamine is prepared by reacting 2,6-dichlorobenzaldehyde with isopropylamine. Pharmaceutical compositions having anticonvulsant, analgesic or anaesthetic activity and the ability to boost the sedative activity of other active substances comprise, as active ingredient, a 1,1-dioxido-thiazolidin-4-one (A or B), together with a suitable carrier. Reference has been directed by the Comptroller to Specification 1,345,159.
GB5603172A 1971-12-06 1972-12-05 1,1-dioxidothiazolidin-4-ones and processes for their manufacture Expired GB1409898A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1772771A CH548411A (en) 1971-12-06 1971-12-06 PROCESS FOR THE PRODUCTION OF NEW 1,1-DIOXOTHIAZOLIDIN4-ONES.

Publications (1)

Publication Number Publication Date
GB1409898A true GB1409898A (en) 1975-10-15

Family

ID=4427629

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5603172A Expired GB1409898A (en) 1971-12-06 1972-12-05 1,1-dioxidothiazolidin-4-ones and processes for their manufacture

Country Status (5)

Country Link
JP (1) JPS4864068A (en)
CH (1) CH548411A (en)
DE (1) DE2259222A1 (en)
FR (1) FR2162488B1 (en)
GB (1) GB1409898A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4176198A (en) 1977-10-06 1979-11-27 William H. Rorer, Inc. Method of treatment
US6174908B1 (en) 1999-05-10 2001-01-16 Icagen, Inc. Potassium channel inhibitors
WO2002009706A1 (en) * 2000-07-27 2002-02-07 Smithkline Beecham Corporation Agonists of follicle stimulating hormone activity
US6395730B1 (en) 1998-06-05 2002-05-28 Icagen, Inc. Potassium channel inhibitors
US7169782B2 (en) 2001-07-16 2007-01-30 Euro-Celtique S.A. Aryl substituted thiazolidinones and the use thereof
US20170253569A1 (en) * 2016-03-07 2017-09-07 National Health Research Institutes Thiazolidinone compounds and use thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1229337A (en) * 1982-04-02 1987-11-17 Pieter T. Haken Fungicidal heterocyclic compounds
US4664694A (en) * 1985-04-24 1987-05-12 Uniroyal Chemical Company, Inc. Substituted thiazolidinones useful as plant growth regulators

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4176198A (en) 1977-10-06 1979-11-27 William H. Rorer, Inc. Method of treatment
US6395730B1 (en) 1998-06-05 2002-05-28 Icagen, Inc. Potassium channel inhibitors
US6174908B1 (en) 1999-05-10 2001-01-16 Icagen, Inc. Potassium channel inhibitors
WO2002009706A1 (en) * 2000-07-27 2002-02-07 Smithkline Beecham Corporation Agonists of follicle stimulating hormone activity
US7169782B2 (en) 2001-07-16 2007-01-30 Euro-Celtique S.A. Aryl substituted thiazolidinones and the use thereof
US20170253569A1 (en) * 2016-03-07 2017-09-07 National Health Research Institutes Thiazolidinone compounds and use thereof
US10544113B2 (en) * 2016-03-07 2020-01-28 National Health Research Institute Thiazolidinone compounds and use thereof

Also Published As

Publication number Publication date
FR2162488B1 (en) 1974-01-04
JPS4864068A (en) 1973-09-05
DE2259222A1 (en) 1973-06-20
CH548411A (en) 1974-04-30
FR2162488A1 (en) 1973-07-20

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Legal Events

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