GB1019563A - Octahydroanthracenes and preparation thereof - Google Patents

Octahydroanthracenes and preparation thereof

Info

Publication number
GB1019563A
GB1019563A GB643164A GB643164A GB1019563A GB 1019563 A GB1019563 A GB 1019563A GB 643164 A GB643164 A GB 643164A GB 643164 A GB643164 A GB 643164A GB 1019563 A GB1019563 A GB 1019563A
Authority
GB
United Kingdom
Prior art keywords
octahydroanthracene
conh
chloro
methoxy
trioxo
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
GB643164A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
Charles Pfizer and Co Inc
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 Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB1019563A publication Critical patent/GB1019563A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/005—Amines or imines
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

A process for the preparation of compounds having the basic skeletal structure of <FORM:1019563/C2/1> comprises reacting a 3,4,10-trioxo-octahydroanthracene having the basic skeletal structure of <FORM:1019563/C2/2> or a tautomer thereof, and an excess of sodium borohydride at a temperature below 0 DEG C. in a reaction inert solvent, e.g. liquid amine, in which R1 is COOR2 or <FORM:1019563/C2/3> wherein R2 is lower alkyl, hydrogen or benzyl; Y1 is H, -CONH(CH3), -CONH(C2H5), -CONH2, cyano, carboxy, lower carbalkoxy, carbobenzoxy; Y2 is -CONH(CH3), -CONH-(C2H5)2, -CONH2, -CON(CH3)2, lower carbalkoxy cyano, carbobenzoxy carboxy; R3 and R4 when taken together with the N atom form a heterocyclic ring consisting of piperazyl, piperidyl, morpholinyl, pyrryl, pyrrolidyl, 2-(lower carbalkoxy), pyrrolidyl or thiomorpholinyl, or when taken separately are each H, aralkyl, amino, mono- and di-alkyl amino, acyl, phenyl or amino substituted phenyl or CH2B1, where B1 is H, lower alkyl, lower carbalkoxy, or mono substituted lower alkyl. In an example n-butyl - 3 - hydroxy - 5 - methoxy - 8 - chloro - 4,10 - dioxo - 1,2,3,4,4a,9,9a,10 - octahydroanthracene - 2 - (a - dimethylamino)acetate hydrochloride, is prepared by reacting 2-carbobutoxymethylidene - 3,4,10 - trioxo - 5 - methoxy - 8 - chloro - 1,2,3,4,4a,9,9a,10 - octahydroanthracene with dimethyl aniline. In another example 2 - [(51 - (31 - N,N - dimethyl - carboxamido - isoxazolyl)(N,N - dimethylamino)-methyl] - 3 - hydroxy - 5 - methoxy - 8 - chloro - 4,10 - dioxo - 1,2,3,4,4a,9,9a,10 - octahydroanthracene is produced by reacting 2-[(51-(31-carbomethoxy)isoxazolyl)methylidene] -5-methoxy - 8 chloro - 3,4,10 - trioxo - 1,2,3,4,4a,9,9a,10 - octahydroanthracene with dimethyl aniline. Many examples are given.
GB643164A 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof Expired GB1019563A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US13301161A 1961-08-18 1961-08-18
US13230461A 1961-08-18 1961-08-18
US20926862A 1962-07-11 1962-07-11
US20926962A 1962-07-11 1962-07-11

Publications (1)

Publication Number Publication Date
GB1019563A true GB1019563A (en) 1966-02-09

Family

ID=27494960

Family Applications (5)

Application Number Title Priority Date Filing Date
GB2988062A Expired GB973022A (en) 1961-08-18 1962-08-03 New acetyl malonamates
GB2987962A Expired GB1013906A (en) 1961-08-18 1962-08-03 Cyclization process and product
GB643064A Expired GB1019562A (en) 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof
GB643164A Expired GB1019563A (en) 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof
GB2987862A Expired GB1013576A (en) 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB2988062A Expired GB973022A (en) 1961-08-18 1962-08-03 New acetyl malonamates
GB2987962A Expired GB1013906A (en) 1961-08-18 1962-08-03 Cyclization process and product
GB643064A Expired GB1019562A (en) 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2987862A Expired GB1013576A (en) 1961-08-18 1962-08-03 Octahydroanthracenes and preparation thereof

Country Status (2)

Country Link
DE (3) DE1470150A1 (en)
GB (5) GB973022A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440503A1 (en) * 1990-02-02 1991-08-07 Syntex (U.S.A.) Inc. 4-Isoxazolecarboxamide derivatives
US7763735B2 (en) 2006-10-11 2010-07-27 President And Fellows Of Harvard College Synthesis of enone intermediate
US8486921B2 (en) 2006-04-07 2013-07-16 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US8598148B2 (en) 2004-05-21 2013-12-03 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US9073829B2 (en) 2009-04-30 2015-07-07 President And Fellows Of Harvard College Synthesis of tetracyclines and intermediates thereto

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2492374A1 (en) * 1980-10-21 1982-04-23 Clin Midy Pyrrolyl di:alkylamino alkylamide(s) - active as myocardial protection agents against arrhythmias and platelet aggregation
EP0054593B1 (en) * 1980-12-18 1985-03-13 Sanofi S.A. Myocardium protecting pyrrole derivatives with anti-arythmic and anti-platelet aggregation activity, process for their preparation and medicines containing them

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440503A1 (en) * 1990-02-02 1991-08-07 Syntex (U.S.A.) Inc. 4-Isoxazolecarboxamide derivatives
US9365493B2 (en) 2004-05-21 2016-06-14 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US8598148B2 (en) 2004-05-21 2013-12-03 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US9884830B2 (en) 2004-05-21 2018-02-06 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US10669244B2 (en) 2004-05-21 2020-06-02 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US11192866B2 (en) 2004-05-21 2021-12-07 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US8486921B2 (en) 2006-04-07 2013-07-16 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
US7960559B2 (en) 2006-10-11 2011-06-14 President And Fellows Of Harvard College Synthesis of enone intermediate
US8293920B2 (en) 2006-10-11 2012-10-23 President And Fellows Of Harvard College Synthesis of enone intermediate
US8580969B2 (en) 2006-10-11 2013-11-12 President And Fellows Of Harvard College Synthesis of enone intermediate
US8907104B2 (en) 2006-10-11 2014-12-09 President And Fellows Of Harvard College Synthesis of enone intermediate
US7763735B2 (en) 2006-10-11 2010-07-27 President And Fellows Of Harvard College Synthesis of enone intermediate
US9073829B2 (en) 2009-04-30 2015-07-07 President And Fellows Of Harvard College Synthesis of tetracyclines and intermediates thereto
US9688644B2 (en) 2009-04-30 2017-06-27 President And Fellows Of Harvard College Synthesis of Tetracyclines and intermediates thereto

Also Published As

Publication number Publication date
DE1470171A1 (en) 1969-04-17
GB1013576A (en) 1965-12-15
GB1019562A (en) 1966-02-09
GB1013906A (en) 1965-12-22
GB973022A (en) 1964-10-21
DE1470150A1 (en) 1969-07-17
DE1468466A1 (en) 1969-03-13

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