GB1310520A - 2-substituted adamantane derivatives and their preparation - Google Patents

2-substituted adamantane derivatives and their preparation

Info

Publication number
GB1310520A
GB1310520A GB4206869A GB1310520DA GB1310520A GB 1310520 A GB1310520 A GB 1310520A GB 4206869 A GB4206869 A GB 4206869A GB 1310520D A GB1310520D A GB 1310520DA GB 1310520 A GB1310520 A GB 1310520A
Authority
GB
United Kingdom
Prior art keywords
adamantane
general formula
group
reaction
acid addition
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
GB4206869A
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.)
Lilly Industries Ltd
Original Assignee
Lilly Industries Ltd
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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Publication of GB1310520A publication Critical patent/GB1310520A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1310520 2-Substituted adamantanes LILLY INDUSTRIES Ltd 20 Aug 1970 [22 Aug 1969] 42068/69 Heading C2C Novel 2-substituted adamantanes of the general formula wherein R is a hydrogen atom or methyl group, either R<SP>1</SP> is a hydrogen atom and Z is a -(CH 2 ) 3 NR<SP>2</SP>R<SP>3</SP> group or R<SP>1</SP> and Z together form a = CH(CH 2 ) 2 NR<SP>2</SP>R<SP>3</SP> group and R<SP>2</SP> and R<SP>3</SP> are each a hydrogen atom or an alkyl group, and acid addition salts thereof, are prepared by reaction of a 2-(3-halopropylidene)-adamantane of the general formula wherein Hal is a halogen atom, with an amine of the general formula R<SP>2</SP>R<SP>3</SP>NH or an acid addition salt thereof and, when Z is a group, hydrogenation of the product. 2 - (3 - Chloropropylidene) - adamantane is prepared by reaction of 2-adamantanone with a lithium derivative of 1-bromo-3-(2-tetrahydropyranyloxy)-propane, followed by hydrolysis, reaction of the resulting 2-hydroxy-2-(3-tetrahydropyran - 2 - yloxyprop - 1 - yl) - adamantane with acetic anhydride, hydrolysis of the 2-(3- acetoxypropylidene)-adamantane so obtained and treatment of the 2-(3-hydroxypropylidiene)- adamantane thus produced with thionyl chloride. Pharmaceutical compositions having antidepressant activity comprise, as active ingredient, a 2-substituted adamantane of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutically acceptable carrier therefor, and may be administered orally, rectally or by injection.
GB4206869A 1969-08-22 1969-08-22 2-substituted adamantane derivatives and their preparation Expired GB1310520A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4206869 1969-08-22

Publications (1)

Publication Number Publication Date
GB1310520A true GB1310520A (en) 1973-03-21

Family

ID=10422693

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4206869A Expired GB1310520A (en) 1969-08-22 1969-08-22 2-substituted adamantane derivatives and their preparation

Country Status (1)

Country Link
GB (1) GB1310520A (en)

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees