GB1146272A - Novel thebaine and oripavine derivatives - Google Patents

Novel thebaine and oripavine derivatives

Info

Publication number
GB1146272A
GB1146272A GB2194/66A GB219466A GB1146272A GB 1146272 A GB1146272 A GB 1146272A GB 2194/66 A GB2194/66 A GB 2194/66A GB 219466 A GB219466 A GB 219466A GB 1146272 A GB1146272 A GB 1146272A
Authority
GB
United Kingdom
Prior art keywords
carbons
substituted
group
aryl
dehydro
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
GB2194/66A
Inventor
Kenneth Walter Bentley
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.)
Reckitt and Sons Ltd
Original Assignee
Reckitt and Sons 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 Reckitt and Sons Ltd filed Critical Reckitt and Sons Ltd
Priority to GB2194/66A priority Critical patent/GB1146272A/en
Priority to NL6700612A priority patent/NL6700612A/xx
Priority to LU52808D priority patent/LU52808A1/xx
Priority to BE692664D priority patent/BE692664A/xx
Priority to ES0335707A priority patent/ES335707A1/en
Priority to FR91484A priority patent/FR1517875A/en
Publication of GB1146272A publication Critical patent/GB1146272A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,146,272. Thebaine and oripavine derivatives. RECKITT & SONS Ltd. 17 Jan., 1967 [17 Jan., 1966], No. 2194/66. Heading C2C. Novel compounds of the general formula (and acid salts thereof) wherein Y is an etheno (-CH=CH-) or ethano (-CH 2 -CH 2 ) group; R and R<SP>1</SP> are both H, Me, Et, Pr, the group C n H 2n+1 CO- (n is 1, 2 or 3), benzoyl or nicotinoyl, provided that when R is H, R<SP>1</SP> is also H and that when R is acyl, R<SP>1</SP> is the same acyl group; R<SP>2</SP> is H, acetonyl, phenacyl, alkyl, alkenyl or alkynyl, which alkyl, alkenyl or alkynyl groups may contain up to 8 carbons and may be substituted on carbons 1 to 5 (the carbon numbered 1 being adjacent to the nitrogen atom) by alicyclic, aryl, substituted aryl, alkoxy, aryloxy, substituted aryloxy, heterocyclic, or substituted amino groups; R<SP>3</SP> is alkyl, alkenyl or alkynyl with up to 3 carbons, an aryl or substituted aryl group; R<SP>4</SP> is an alkyl, alkenyl or alkynyl group with up to 8 carbons and which may be substituted on carbons 1 to 4 (the carbon numbered 1 being adjacent to the carbon atoms having the double bond) by alicyclic, aryl, substituted aryl, alkoxy, aryloxy or substituted aryloxy groups or R<SP>4</SP> is an alicyclic group containing 3 to 7 carbons, are prepared by acid hydrolysis, with or without dehydration, of 5,14-etheno- or 5,14-ethano-thebaine or oripavine derivatives possessing the appropriate tertiary alcoholic group (-COH.R<SP>3</SP>R<SP>4</SP>) at the 7-position. Pharmaceutical compositions which affect the central nervous system contain as the active ingredient the above novel compounds in association with a carrier and the compositions are in unit dosage form. 4,6 - Dehydro - 6 - o - methyl - 5,14 - (1 - 2<SP>1</SP>- hydroxyprop - 21 - ylethano) thebainiol is prepared by the interaction of 4,6-dehydro-6-o-methyl- 5,14 - (1 - acetylethano) thebainol and methyl lithium. 5,7 - Dehydro - 4,6 - o - dimethyl - 6,14 - endoetheno - 7 - (2 - hydroxyprop - 2 - yl) - dihydrothebainol is prepared by the interaction of 5,7 - dehydro - 4,6 - o - dimethyl-6,14-endoetheno - 7 - acetyldihydrothebainol and methyl magnesium iodide.
GB2194/66A 1966-01-17 1966-01-17 Novel thebaine and oripavine derivatives Expired GB1146272A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB2194/66A GB1146272A (en) 1966-01-17 1966-01-17 Novel thebaine and oripavine derivatives
NL6700612A NL6700612A (en) 1966-01-17 1967-01-13
LU52808D LU52808A1 (en) 1966-01-17 1967-01-13
BE692664D BE692664A (en) 1966-01-17 1967-01-16
ES0335707A ES335707A1 (en) 1966-01-17 1967-01-16 Procedure for the preparation of derivatives of the theory (Machine-translation by Google Translate, not legally binding)
FR91484A FR1517875A (en) 1966-01-17 1967-01-17 Process for the preparation of thebaine and oripavine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2194/66A GB1146272A (en) 1966-01-17 1966-01-17 Novel thebaine and oripavine derivatives

Publications (1)

Publication Number Publication Date
GB1146272A true GB1146272A (en) 1969-03-26

Family

ID=9735246

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2194/66A Expired GB1146272A (en) 1966-01-17 1966-01-17 Novel thebaine and oripavine derivatives

Country Status (6)

Country Link
BE (1) BE692664A (en)
ES (1) ES335707A1 (en)
FR (1) FR1517875A (en)
GB (1) GB1146272A (en)
LU (1) LU52808A1 (en)
NL (1) NL6700612A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1164672A (en) * 1967-03-31 1969-09-17 Reckitt & Sons Ltd Novel Derivatives of Thebaine and Oripavine, their Pharmaceutically Acceptable Salts, and to processes of their production
GB1164671A (en) * 1967-03-31 1969-09-17 Reckitt & Sons Ltd Novel Derivatives of Thebaine and Oripavine to their Salts, and to processes for their preparation
DE2230154A1 (en) * 1972-06-21 1974-01-17 Boehringer Sohn Ingelheim N- (HETEROARYL-METHYL) -6,14-ENDOAETHENO7ALPHA-HYDROXYALKYL-TETRAHYDRO-NORORIPAVIN AND -THEBAINE, THEIR HYDROGENATION PRODUCTS AND ACID ADDITIONAL SALTS AND THE PROCESS FOR THEIR PRODUCTION

Also Published As

Publication number Publication date
BE692664A (en) 1967-07-03
LU52808A1 (en) 1967-03-13
ES335707A1 (en) 1967-12-16
NL6700612A (en) 1967-07-18
FR1517875A (en) 1968-03-22

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