FR2034448A1 - Benzoxazocine derivs cns active - Google Patents

Benzoxazocine derivs cns active

Info

Publication number
FR2034448A1
FR2034448A1 FR7011119A FR7011119A FR2034448A1 FR 2034448 A1 FR2034448 A1 FR 2034448A1 FR 7011119 A FR7011119 A FR 7011119A FR 7011119 A FR7011119 A FR 7011119A FR 2034448 A1 FR2034448 A1 FR 2034448A1
Authority
FR
France
Prior art keywords
tetrahydro
hydrogen
soln
chloroform
dimethyl
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.)
Granted
Application number
FR7011119A
Other languages
French (fr)
Other versions
FR2034448B1 (en
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 FR6904419A external-priority patent/FR2002482A1/fr
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of FR2034448A1 publication Critical patent/FR2034448A1/en
Application granted granted Critical
Publication of FR2034448B1 publication Critical patent/FR2034448B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

Landscapes

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

Abstract

Method for the prepn. of 3,4,5,6-tetrahydro-2,6-methano-2H-1,5-benzoxazocine derivs. of the general formula (I) and acid addn. salts and N-oxides of (I) R1 = hydrogen or alkyl (1-6C) R2 = hydrogen, opt. substd. hydrocarbon (1 to 24C) or acyl R3 = hydrogen, opt. substd. aliphatic or arylaliphatic hydrocarbon (1 to 24C) X = hydrogen or hydroxy, or an ester or ether deriv. of hydroxy The cpds. have C.N.S. activity esp. analgetic activity and have activity on the heart- and blood-fat system. A soln. of 0.4 g. of a mixture of 2-(1,4-dimethyl-1,2,5,6-tetrahydro-2-pyridinyl)-resorcinol and 2-(1,4-dimethyl-1,2,3,6-tetrahydro-2-pyridinyl)-resorcinol was boiled for 1 hr. on a water bath with 10 ml. conc. hydrochloric acid. The soln. was cooled and neutralised to pH 7 with 10% NaOH soln. The mixture was extracted with chloroform (2 X 100 ml) and the extract washed with satd. NaCl soln. and after drying, evaporated to dryness. The residual brown gum was chromatographed on a column of silica gel (20 g.) eluting with chloroform, chloroform/methanol and finally with methanol, the methanol eluate on evaporation yielding 0.18 g. 2,5-dimethyl-3,4,5,6-tetrahydro-2,6-methano-2H-1,5-benzoxazocin -7-ol, as a dark brown foam.
FR7011119A 1968-02-23 1970-03-27 Benzoxazocine derivs cns active Granted FR2034448A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70744868A 1968-02-23 1968-02-23
FR6904419A FR2002482A1 (en) 1968-02-23 1969-02-21

Publications (2)

Publication Number Publication Date
FR2034448A1 true FR2034448A1 (en) 1970-12-11
FR2034448B1 FR2034448B1 (en) 1974-08-09

Family

ID=26214855

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7011119A Granted FR2034448A1 (en) 1968-02-23 1970-03-27 Benzoxazocine derivs cns active

Country Status (1)

Country Link
FR (1) FR2034448A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2518093A2 (en) * 1980-12-15 1983-06-17 Roussel Uclaf 3-1,2,5,6-Tetra:hydro-1-substd.-3-pyridyl phenol derivs. - dopaminergic agonists and/or antagonists and antiemetics, used to treat Parkinson's disease, psychic disorders etc.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NEANT *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2518093A2 (en) * 1980-12-15 1983-06-17 Roussel Uclaf 3-1,2,5,6-Tetra:hydro-1-substd.-3-pyridyl phenol derivs. - dopaminergic agonists and/or antagonists and antiemetics, used to treat Parkinson's disease, psychic disorders etc.

Also Published As

Publication number Publication date
FR2034448B1 (en) 1974-08-09

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Legal Events

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