GB1066613A - Naphthalene derivatives - Google Patents

Naphthalene derivatives

Info

Publication number
GB1066613A
GB1066613A GB9092/65A GB909265A GB1066613A GB 1066613 A GB1066613 A GB 1066613A GB 9092/65 A GB9092/65 A GB 9092/65A GB 909265 A GB909265 A GB 909265A GB 1066613 A GB1066613 A GB 1066613A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
naphthalene nucleus
radical
stands
radicals
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
GB9092/65A
Inventor
Peter Anthony Bond
Bernard Joseph Mcloughlin
Leslie Harold Smith
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB9092/65A priority Critical patent/GB1066613A/en
Priority to NO161543A priority patent/NO115028B/no
Priority to DE19661543685 priority patent/DE1543685A1/en
Priority to IL25132A priority patent/IL25132A/en
Priority to NL6601686A priority patent/NL6601686A/xx
Priority to SE1873/66A priority patent/SE316191B/xx
Priority to FI660373A priority patent/FI44622C/en
Priority to ES0323083A priority patent/ES323083A1/en
Priority to BE676821D priority patent/BE676821A/xx
Priority to AT438067A priority patent/AT264511B/en
Priority to AT437967A priority patent/AT264510B/en
Priority to AT164866A priority patent/AT264509B/en
Priority to AT438167A priority patent/AT264512B/en
Priority to AT438367A priority patent/AT264504B/en
Priority to AT438267A priority patent/AT264513B/en
Priority to CH900169A priority patent/CH479540A/en
Priority to CH899969A priority patent/CH487838A/en
Priority to CH900069A priority patent/CH485662A/en
Priority to CH1928569A priority patent/CH491079A/en
Priority to CH276766A priority patent/CH486420A/en
Priority to BR177439/66A priority patent/BR6677439D0/en
Priority to FR51870A priority patent/FR1470602A/en
Priority to DK111866AA priority patent/DK122274B/en
Priority to FR63857A priority patent/FR5516M/fr
Publication of GB1066613A publication Critical patent/GB1066613A/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
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Compounds of the general Formula (I) <FORM:1066613/C2/1> (wherein R1 stands for a hydrogen atom, an alkyl radical optionally substituted by one or more hydroxy, alkoxy or aryloxy radicals, a cycloalkyl radical or an aralkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms, and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents), their esters (other than those wherein the naphthalene nucleus bears a hydroxy radical) and the acid addition salts of the alcohols and esters are prepared by (a)-in the case of those alcohols wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals-reacting a compound of the formula <FORM:1066613/C2/2> (wherein A stands for the group <FORM:1066613/C2/3> or <FORM:1066613/C2/4> wherein X stands for a halogen atom, and wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with R1NH2 (when R1 stands for a hydrogen atom the ammonia may be replaced by phthalimide, the phthalic acid residue being subsequently removed), (b)-in the case of those alcohols wherein the naphthalene nucleus bears at least one hydroxy radical-reacting a compound of the Formula (I) wherein the naphthalene nucleus bears at least one alkoxy substituent and may optionally bear one or more alkyl substituents, or an acid addition salt thereof, with a dealkylating agent, (c)-in the case of those alcohols wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals -reacting a compound of the formula <FORM:1066613/C2/5> (wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with a compound of the formula <FORM:1066613/C2/6> or <FORM:1066613/C2/7> (d)-in the case of those alcohols wherein R1 stands for a radical of the formula -CHR3R4, wherein R3 stands for a hydrogen atom or an alkyl radical and R4 stands for an alkyl radical optionally substituted by one or more hydroxy, alkoxy or aryloxy radicals, or an aryl or aralkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms, or R3 and R4 are joined together with the adjacent carbon atom to form a cycloalkyl radical-reacting a compound (which may be generated in situ) of the formula <FORM:1066613/C2/8> (wherein the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with R3COR4 under reducing conditions, (e)-in the case of those alcohols wherein R1 is as defined above except that it is not an a -aryl-alkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms-hydrogenolysing a compound of the formula <FORM:1066613/C2/9> (wherein R5 stands for a hydrogenolysable radical and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) or an acid addition salt thereof, or (f)-in the case of the esters-acylating an acid addition salt of a corresponding alcohol (when the ester bears an acyloxy radical on the naphthalene nucleus, the term "corresponding alcohol" includes the alcohol wherein the naphthalene nucleus bears a hydroxy radical), optionally followed in each case by acid addition salt formation or conversion to the free base. Oxazolidine derivatives of the general formula <FORM:1066613/C2/10> (wherein R6 stands for a hydrogen atom or an alkyl radical and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) and their acid addition salts are prepared by reacting a compound of the Formula (I) with R6CHO, optionally followed by acid addition salt formation. The preparation of 1,2-epoxy-3-(4-methoxy-1-naphthoxy)propane, 1 - chloro - 3 - (6,7 - dimethoxy - 1 - naphthoxy) - 2 - propanol, 1 - (N - benzyl - N - isopropylamino) - 3 - (4 - methoxy - 1 - naphthoxy) - 2 - propanol hydrochloride, 1 - phthalimido - 3 - (4 - methoxy - 1 - naphthoxy) - 2 - propanol, 1,2 - epoxy - 3 - (5 - methoxy - 1 - naphthoxy) - propane, 1 - chloro - 3 - (6 - methoxy - 1 - naphthoxy) - 2 - propanol, 1 - (4 - acetoxy - 3 - methyl - 1 - naphthoxy) - 3 - chloro - 2 - propanol, 4 - acetoxy - 3 - methyl - 1 - naphthol and 1,2 - epoxy - 3 - (4 - isopropoxy - 1 - naphthoxy)propane is described. Compounds (I), their esters and oxazolidine derivatives and the acid addition salts of the alcohols, esters and oxazolidine derivatives, are useful in the treatment or prophylaxis of heart diseases and in the treatment of hypertension, myocardial infraction and phaeochromocytoma. They may be administered in the form of pharmaceutical preparations containing them together with a diluent or carrier.
GB9092/65A 1965-03-03 1965-03-03 Naphthalene derivatives Expired GB1066613A (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
GB9092/65A GB1066613A (en) 1965-03-03 1965-03-03 Naphthalene derivatives
NO161543A NO115028B (en) 1965-03-03 1966-02-02
DE19661543685 DE1543685A1 (en) 1965-03-03 1966-02-04 Process for the preparation of naphthalene derivatives
IL25132A IL25132A (en) 1965-03-03 1966-02-07 1-naphthyloxy-3-(substituted amino)-2-propanols
NL6601686A NL6601686A (en) 1965-03-03 1966-02-10
SE1873/66A SE316191B (en) 1965-03-03 1966-02-14
FI660373A FI44622C (en) 1965-03-03 1966-02-15 Process for the preparation of therapeutically valuable substituted naphthalene derivatives.
ES0323083A ES323083A1 (en) 1965-03-03 1966-02-15 Procedure for the manufacture of naftalene derivatives. (Machine-translation by Google Translate, not legally binding)
BE676821D BE676821A (en) 1965-03-03 1966-02-21
AT438067A AT264511B (en) 1965-03-03 1966-02-22 Process for the production of new basic naphthol ethers and their acid addition salts
AT437967A AT264510B (en) 1965-03-03 1966-02-22 Process for the production of new basic naphthol ethers and their acid addition salts
AT164866A AT264509B (en) 1965-03-03 1966-02-22 Process for the production of new basic naphthol ethers and their acid addition salts
AT438167A AT264512B (en) 1965-03-03 1966-02-22 Process for the production of new basic naphthol ethers and their acid addition salts
AT438367A AT264504B (en) 1965-03-03 1966-02-22 Process for the preparation of new basic esters and their acid addition salts
AT438267A AT264513B (en) 1965-03-03 1966-02-22 Process for the production of new basic naphthol ethers and their acid addition salts
CH900169A CH479540A (en) 1965-03-03 1966-02-25 Process for the preparation of α-naphthol derivatives
CH899969A CH487838A (en) 1965-03-03 1966-02-25 Process for the preparation of α-naphthol derivatives
CH900069A CH485662A (en) 1965-03-03 1966-02-25 Process for the preparation of α-naphthol derivatives
CH1928569A CH491079A (en) 1965-03-03 1966-02-25 Process for the preparation of α-naphthol derivatives
CH276766A CH486420A (en) 1965-03-03 1966-02-25 Process for the preparation of α-naphthol derivatives
BR177439/66A BR6677439D0 (en) 1965-03-03 1966-03-01 HOMOCYCLICAL COMPOUNDS
FR51870A FR1470602A (en) 1965-03-03 1966-03-03 Naphthalene compounds and their manufacturing process
DK111866AA DK122274B (en) 1965-03-03 1966-03-03 Analogous process for the preparation of therapeutically active naphthoxypropanolamine derivatives or salts thereof.
FR63857A FR5516M (en) 1965-03-03 1966-06-02

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9092/65A GB1066613A (en) 1965-03-03 1965-03-03 Naphthalene derivatives

Publications (1)

Publication Number Publication Date
GB1066613A true GB1066613A (en) 1967-04-26

Family

ID=9865202

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9092/65A Expired GB1066613A (en) 1965-03-03 1965-03-03 Naphthalene derivatives

Country Status (14)

Country Link
AT (6) AT264509B (en)
BE (1) BE676821A (en)
BR (1) BR6677439D0 (en)
CH (1) CH486420A (en)
DE (1) DE1543685A1 (en)
DK (1) DK122274B (en)
ES (1) ES323083A1 (en)
FI (1) FI44622C (en)
FR (1) FR5516M (en)
GB (1) GB1066613A (en)
IL (1) IL25132A (en)
NL (1) NL6601686A (en)
NO (1) NO115028B (en)
SE (1) SE316191B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2644833A1 (en) * 1976-10-05 1978-04-20 Boehringer Sohn Ingelheim NEW 1-ARYLOXY-2-HYDROXY-3-ALKYLENE AMINOPROPANES AND METHOD FOR THE PRODUCTION THEREOF
US4376125A (en) * 1980-11-05 1983-03-08 University Of Virginia Alumni Patents Foundation Aminobenzlpropranolol and pharmaceutical preparation thereof
CN114224875A (en) * 2021-11-04 2022-03-25 中南大学湘雅医院 New application of alcohol compound and antitumor drug

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8542005B2 (en) 2010-04-28 2013-09-24 Teradyne, Inc. Connecting digital storage oscilloscopes
US8502522B2 (en) 2010-04-28 2013-08-06 Teradyne, Inc. Multi-level triggering circuit
US8098181B2 (en) 2010-04-28 2012-01-17 Teradyne, Inc. Attenuator circuit
US8531176B2 (en) 2010-04-28 2013-09-10 Teradyne, Inc. Driving an electronic instrument

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2644833A1 (en) * 1976-10-05 1978-04-20 Boehringer Sohn Ingelheim NEW 1-ARYLOXY-2-HYDROXY-3-ALKYLENE AMINOPROPANES AND METHOD FOR THE PRODUCTION THEREOF
US4376125A (en) * 1980-11-05 1983-03-08 University Of Virginia Alumni Patents Foundation Aminobenzlpropranolol and pharmaceutical preparation thereof
CN114224875A (en) * 2021-11-04 2022-03-25 中南大学湘雅医院 New application of alcohol compound and antitumor drug
CN114224875B (en) * 2021-11-04 2023-08-11 中南大学湘雅医院 New use of alcohol compound and antitumor drug

Also Published As

Publication number Publication date
DE1543685A1 (en) 1969-12-18
AT264509B (en) 1968-09-10
ES323083A1 (en) 1967-01-01
BR6677439D0 (en) 1973-09-18
NL6601686A (en) 1966-09-05
FI44622B (en) 1971-08-31
AT264510B (en) 1968-09-10
IL25132A (en) 1969-11-30
FI44622C (en) 1971-12-10
FR5516M (en) 1967-11-06
AT264513B (en) 1968-09-10
SE316191B (en) 1969-10-20
NO115028B (en) 1968-07-08
AT264511B (en) 1968-09-10
DK122274B (en) 1972-02-14
AT264512B (en) 1968-09-10
BE676821A (en) 1966-08-22
AT264504B (en) 1968-09-10
CH486420A (en) 1970-02-28

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