GB1015026A - New derivatives of 2-oxazolidinone and the preparation thereof - Google Patents

New derivatives of 2-oxazolidinone and the preparation thereof

Info

Publication number
GB1015026A
GB1015026A GB1238163A GB1238163A GB1015026A GB 1015026 A GB1015026 A GB 1015026A GB 1238163 A GB1238163 A GB 1238163A GB 1238163 A GB1238163 A GB 1238163A GB 1015026 A GB1015026 A GB 1015026A
Authority
GB
United Kingdom
Prior art keywords
prepared
given
formula
acid
bicycloalkanes
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
GB1238163A
Inventor
Gilbert Regnier
Roger Canevari
Jean-Claude Le Douarec
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.)
Science Union et Cie
Original Assignee
Science Union et Cie
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
Priority claimed from FR857672A external-priority patent/FR1301267A/en
Priority to GB12746/62A priority Critical patent/GB974134A/en
Priority to GB1238163A priority patent/GB1015026A/en
Application filed by Science Union et Cie filed Critical Science Union et Cie
Priority to BE645036A priority patent/BE645036A/xx
Priority to CH380164A priority patent/CH423781A/en
Priority to BR157904/64A priority patent/BR6457904D0/en
Priority to DE19641470275 priority patent/DE1470275C/en
Priority to ES298088A priority patent/ES298088A2/en
Priority to FR968836A priority patent/FR1395085A/en
Priority to US355069A priority patent/US3193560A/en
Priority to FR979462A priority patent/FR3480M/en
Publication of GB1015026A publication Critical patent/GB1015026A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1015026/C2/1> (wherein <FORM:1015026/C2/2> is a mono- or bicylic-unsubstituted saturated carbocyclic ring of 7 to 10 carbon atoms or a substituted mono- or bicyclic-saturated carbocyclic ring of 6 carbon atoms, the substituents being selected from halogen atoms, a hydroxyl group and alkyl and alkoxy radicals; X is O or NH; and Z is a dialkylamino group) and acid-addition salts thereof; and their preparation by reacting the compound HX-(CH2)2-Z with an acid chloride of the formula <FORM:1015026/C2/3> The compounds of the invention have a number of stereoisomeric forms, and given forms may be obtained by using given stereoisomeric acid chlorides in the process of the invention. Examples are given. Acid chlorides of the above general formula are prepared from phosgene and the sodium salts of the corresponding N-unsubstituted-oxazolidinones, themselves prepared by cyclizing reaction of substituted hydroxyamines with phosgene or by Curtius rearrangement and cyclization of 1-hydroxy - 1 - aminocarbamoylmethyl - cycloalkanes or bicycloalkanes, themselves prepared from corresponding 1 - hydroxy - 1 - alkoxycarbonylmethyl - cycloalkanes or bicycloalkanes (prepared by Reformatsky's reaction with cycloalkanones or bicycloalkanones). 1 - Aminomethyl - 2 - chloro - 1 - cyclohexanol (hydrochloride described) is prepared by catalytic reduction of 2-chloro-1-nitromethyl-1-cyclohexanol. The oxazolidinone derivatives of the invention, which are stated to possess analgesic and anti-inflammatory activity, may be made up into pharmaceutical compositions with suitable carriers. Tablets, suppositories and solutions are referred to.
GB1238163A 1961-04-04 1963-03-28 New derivatives of 2-oxazolidinone and the preparation thereof Expired GB1015026A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB12746/62A GB974134A (en) 1963-03-28 1962-04-03 Oxazolidinone derivatives
GB1238163A GB1015026A (en) 1961-04-04 1963-03-28 New derivatives of 2-oxazolidinone and the preparation thereof
BE645036A BE645036A (en) 1961-04-04 1964-03-11
CH380164A CH423781A (en) 1963-03-28 1964-03-24 Process for the preparation of new derivatives of oxazolidinone-2
BR157904/64A BR6457904D0 (en) 1963-03-28 1964-03-25 PROCESS FOR THE PREPARATION OF NEW OXAZOLIDINONE-2 DERIVATIVES
DE19641470275 DE1470275C (en) 1963-03-28 1964-03-26 Oxazohdon (2) derivatives and processes for their preparation
US355069A US3193560A (en) 1963-03-28 1964-03-26 New derivatives of 2-oxazolidinone
ES298088A ES298088A2 (en) 1963-03-28 1964-03-26 Procedure for the preparation of new derivatives of oxazolidinone-2 (Machine-translation by Google Translate, not legally binding)
FR968836A FR1395085A (en) 1963-03-28 1964-03-26 New derivatives of oxazolidinone-2 and their preparation processes
FR979462A FR3480M (en) 1963-03-28 1964-06-24 New drugs based on spiro derivatives of oxazolidinone-2.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR857672A FR1301267A (en) 1961-04-04 1961-04-04 New derivatives of oxazolidinone-2 and their preparation methods
FR866961 1961-07-04
GB1238163A GB1015026A (en) 1961-04-04 1963-03-28 New derivatives of 2-oxazolidinone and the preparation thereof

Publications (1)

Publication Number Publication Date
GB1015026A true GB1015026A (en) 1965-12-31

Family

ID=27245932

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1238163A Expired GB1015026A (en) 1961-04-04 1963-03-28 New derivatives of 2-oxazolidinone and the preparation thereof

Country Status (2)

Country Link
BE (1) BE645036A (en)
GB (1) GB1015026A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003073979A2 (en) * 2002-03-07 2003-09-12 Schwarz Pharma Ag Derivatives of azaspiro compounds for the treatment of pain

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003073979A2 (en) * 2002-03-07 2003-09-12 Schwarz Pharma Ag Derivatives of azaspiro compounds for the treatment of pain
WO2003073979A3 (en) * 2002-03-07 2003-12-31 Sanol Arznei Schwarz Gmbh Derivatives of azaspiro compounds for the treatment of pain
US7282515B2 (en) 2002-03-07 2007-10-16 Schwarz Pharma Ag Derivatives of azaspiro compounds for the treatment of pain

Also Published As

Publication number Publication date
BE645036A (en) 1964-09-11

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