GB1268239A - Tricycloundecane derivatives - Google Patents

Tricycloundecane derivatives

Info

Publication number
GB1268239A
GB1268239A GB44373/69A GB4437369A GB1268239A GB 1268239 A GB1268239 A GB 1268239A GB 44373/69 A GB44373/69 A GB 44373/69A GB 4437369 A GB4437369 A GB 4437369A GB 1268239 A GB1268239 A GB 1268239A
Authority
GB
United Kingdom
Prior art keywords
prepared
tricyclo
reaction
methyl
undecane
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
GB44373/69A
Inventor
G H Berezin
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1268239A publication Critical patent/GB1268239A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C07D303/06—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
    • C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/453—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/12—Saturated polycyclic compounds
    • C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
    • C07C61/135—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen 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
    • 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
    • C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
    • C07C2603/78—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing seven-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,268,239. Tricycloundecane derivatives. E.I. DU PONT DE NEMOURS & CO. 8 Sept., 1969 [9 Sept., 1968; 31 July, 1969], No. 44373/69. Heading C2C. [Also in Division C5] Novel compounds I in which Q has Formula II n is 0 or 1; R<SP>1</SP> and R<SP>2</SP> are H or 1-2C alkyl; R 3 is H, 1-4C alkyl, 3-9C alkenyl, 3-methyl-2- methylene - 3 - butenyl, 5-8C cycloalkenyl, 6-9C alkenylcycloalkyl, 6-9C cycloalkylalkenyl, 3-5C alkynyl, or benzyl and R 4 is H, 1-3C alkyl, 3-5C alkenyl or propargyl or R 3 and R 4 together form a divalent organic radical subject to the proviso that any unsaturation in R 3 and R 4 is not in the 1-position and salts thereof are prepared by (a) reducing compounds III in which A is a group capable of being reduced to NH 2 or -CH(R<SP>2</SP>)NH 2 ; (b) reductively aminating a compound III in which A is a group or atom capable of being reductively aminated to a group (c) reductively aminating with NH 3 tricycloundecan-4-ane to give I where n is 0 and R 1 , R 3 and R 4 are all H (d) reacting a compound IV where X is a leaving group with an amine donor (e) reducing a compound V where R<SP>4</SP> and R<SP>5</SP> are H or 1-3C alkyl (f) converting the amino group in I into a different amino group by known methods or (g) hydrolysing a compound VI Spiro[ozirane - 2,2<SP>1</SP>-tricyclo(3.3.1.1<SP>3,7</SP>)]-decane is prepared by oxidation of 2-methyleneadamantane. Adamantane cyanohydrin is prepared by reaction of adamantanone with NaCN. 2 - Aminomethyl - 2 - adamantanol is prepared by reaction of adamantane cyanohydrin with LiAlH 4 or by reaction of the above spiro intermediate with NH 3 in a stainless steel bomb. Novel tricyclo(4.3.1.1.<SP>3,8</SP>)undecan-4-one is prepared by reaction of 2-amino-methyl-2-adamantanol with NaNO 2 and glacial acetic acid. Tricyclo(4.3.1.1.<SP>3,8</SP>)undecan - 4 - one - oxime is prepared by reaction of the 4-one with hydroxylamine HCl. 4 - Formamido - tricyclo(4.3.1.1<SP>3,8</SP>) - undecane is prepared by reaction of the appropriate 4- amino compound with butyl formate. Similarly prepared are 4-formamidomethyl-; 4-methyl-4- formamidomethyl; α - methyl - 4 - formamidomethyl- and N - formyl - N - methyl - 4 - aminomethyl-tricyclo(4.3.1.1.<SP>3,8</SP>)-undecane. N - acetyl - tricyclo(4.3.1.1<SP>3,8</SP>)undecane - 4- amine is prepared by acetylation of the appropriate amine. Similarly prepared are N-acetyl- N - methyl - 4 - amino- ; N - acetyl - N - methyl- 4 - amino - methyl-; N - acetyl - α - methyl - 4- aminomethyl-; N - acetyl N - methyl - 4 - amino- 4 - ethyl-; N - acetyl - N - benzyl - 4 - aminomethyl- and N - acetyl - N - (3 - cyclohexenyl)- 4 - aminomethyl - tricyclo(4.3.1.1.<SP>3,8</SP>) - undecane. 4 - Ethyl - 4 - hydroxy - tricyclo(4.3.1.1<SP>3,8</SP>)- undecane is prepared by reaction of the 4-one with ethyl lithium. The 4-methyl derivative may be similarly prepared. Tricyclo(4.3.1.1.<SP>3,8</SP>)undecan - 4 - ol is prepared by reduction of the 4-one with LiAlH 4 . 4 . Bromo - tricyclo(4.3.1.1<SP>3,8</SP>)undecane is prepared by reaction of the 4-ol with Br 2 . 4 - Methylene - tricyclo(4.3.1.1<SP>3,8</SP>)undecane is prepared by reaction of the 4-one with methyl triphenylphosphonium bromide. 4 - Hydroxymethyl - tricyclo(4.3.1.1<SP>3,8</SP>)undecane is prepared from the 4-methylene derivative by reaction with H 2 O 2 . Tricyclo(4.3.1.1<SP>3,8</SP>)undecane - 4 - carboxylic acid is prepared by oxidation of the 4-hydroxymethyl derivative. The corresponding acid chloride is prepared by conventional methods and converted to the 4-carboxamide by reaction with NH 3 . Similarly prepared are the N-allyl-; N - (1,1 - dimethylallyl)-; N - (3 - methylenecyclobutylmethyl)-; N - (2 - methallyl)- and N- (3 methylenecyclobutyl) - carboxamide derivatives and 3 - methylene - 1 - [tricyclo(4.3.1.1.<SP>3,8</SP>)undecan - 4 - yl . carbonyl] - azetidine. 4 - Cyano - tricyclo(4.3.1.1<SP>3,8</SP>) - undecane is prepared by reaction of the 4-carboxamide derivative with SOCl 2 or by reaction of the 4- bromo derivative with NaCN. Methyl - 4 - tricyclo(4.3.1.1.<SP>3,8</SP>)undecyl ketone is prepared by reaction of the 4 cyano derivative with methyl magnesium bromide. Pharmaceutical compositions comprise a compound I together with a suitable excipient for oral or parenteral administration as anti-viral agents.
GB44373/69A 1968-09-09 1969-09-08 Tricycloundecane derivatives Expired GB1268239A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US75863168A 1968-09-09 1968-09-09
US84662069A 1969-07-31 1969-07-31

Publications (1)

Publication Number Publication Date
GB1268239A true GB1268239A (en) 1972-03-22

Family

ID=27116551

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44373/69A Expired GB1268239A (en) 1968-09-09 1969-09-08 Tricycloundecane derivatives

Country Status (8)

Country Link
JP (1) JPS4813539B1 (en)
BR (1) BR6912297D0 (en)
CH (1) CH529083A (en)
DE (1) DE1945208A1 (en)
FR (1) FR2017657B1 (en)
GB (1) GB1268239A (en)
NL (1) NL6913643A (en)
SE (1) SE373358B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2529025C1 (en) * 2013-04-23 2014-09-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) Method of producing 2,2-adamantylene spirooxirane derivatives

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1435729A (en) * 1972-10-11 1976-05-12 Nard Institute Ltd Alicyclic amino compounds and their production
JPS5273035A (en) * 1975-12-15 1977-06-18 Asahi Kagaku Kenkyusho Device for regenerating fixer
DE2749664B2 (en) * 1977-11-05 1981-01-29 Kloeckner-Werke Ag, 4100 Duisburg Connecting and securing device for the chain conveyor with or without guides for mining machines, in particular for coal
DE3314499C2 (en) * 1983-04-21 1985-08-22 Hermann Hemscheidt Maschinenfabrik Gmbh & Co, 5600 Wuppertal Access device for a longwall
EP0178668A3 (en) * 1984-10-19 1987-03-25 E.I. Du Pont De Nemours And Company Process for preparing rimantadine
DE3511494A1 (en) * 1985-03-29 1986-10-09 Saarbergwerke AG, 6600 Saarbrücken Joint-bridging connection of channel elements of scraper conveyors or their fittings
DE20307151U1 (en) 2003-05-07 2004-07-22 Dbt Gmbh Gag for gag connections and gag connection

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1054275A (en) * 1963-05-01
CH429709A (en) * 1964-03-26 1967-02-15 Geigy Ag J R Process for the preparation of a new tricycloalkanamine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2529025C1 (en) * 2013-04-23 2014-09-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) Method of producing 2,2-adamantylene spirooxirane derivatives

Also Published As

Publication number Publication date
FR2017657B1 (en) 1973-06-08
JPS4813539B1 (en) 1973-04-27
NL6913643A (en) 1970-03-11
BR6912297D0 (en) 1973-05-10
SE373358B (en) 1975-02-03
FR2017657A1 (en) 1970-05-22
DE1945208A1 (en) 1970-03-19
CH529083A (en) 1972-10-15

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