IE39712B1 - 10-bornanamine and 7,7-dimethylnorbornan-1-amine and derivatives - Google Patents

10-bornanamine and 7,7-dimethylnorbornan-1-amine and derivatives

Info

Publication number
IE39712B1
IE39712B1 IE46174A IE46174A IE39712B1 IE 39712 B1 IE39712 B1 IE 39712B1 IE 46174 A IE46174 A IE 46174A IE 46174 A IE46174 A IE 46174A IE 39712 B1 IE39712 B1 IE 39712B1
Authority
IE
Ireland
Prior art keywords
group
nitrogen atom
substituted
compound
amino
Prior art date
Application number
IE46174A
Other versions
IE39712L (en
Original Assignee
Glaxo Lab 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
Priority claimed from GB1089473A external-priority patent/GB1468349A/en
Application filed by Glaxo Lab Ltd filed Critical Glaxo Lab Ltd
Publication of IE39712L publication Critical patent/IE39712L/en
Publication of IE39712B1 publication Critical patent/IE39712B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

This invention relates to a process for the preparation of 7,7dimethyl-2,2,1!-bicycloheptanes having at the 1-positions a group R, and the physiologically acceptable salts thereof, wherein R is an amino or aminomethyl group possessing a basic nitrogen atom and is substituted at the amino nitrogen atom (via a single or double bond) and/or at the 10- carbon atom by one or more C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl groups, which may be unsubstituted or substituted by an amino, mono or dialkylamino,imino, hydroxy, thiol, an esterified or etherified hydroxy or thiol group or (when a basic nitrogen atom is also present on the group) an oxo group in an .alpha.-position in relation to the R nitrogen atom; a C3-8 cyclo-alkyl group; a monocyclic aralkyl, aralkenyl or aralkynyl group; a phenyl group or substituted phenyl group; a 5 or 6 membered heterocyclic aryl group; or wherein the nitrogen atom of R forms part of 4 to 8 membered heterocyclic ring which may be unsubstituted or substituted by a C1-6 alkyl, hydroxy or C3-10 cycloalkyl group or which may be fused to a benzene ring;(a) wherein the group R possesses a methylene group in an .alpha.-position in relation to the 1- or 10- nitrogen atom, which comprises reducing the corresponding amide;(b) wherein R is a methylamino group, which comprises reducing an ??ter of the corresponding carboxyamino compound; (c) wherein R is a methylamino group, which comprises reductively methylating the corresponding primary amine;(d) wherein the 1- or 10- nitrogen atom of R is linked by a double bond to an aliphatic or araliphatic substituent, which comprises condensing the corresponding primary amine with an aldehyde or ketone;(e) wherein the product is 1,3,5-tris-(bornan-10-yl)-1,3,5-hexahydrotriazine, which comprises reacting 10bornanamine with formaldehyde;(f) wherein R is an aminomethyl group in which one of the hydrogen atoms on the methyl carbon atom is substituted, which comprises reducing the corresponding ketoxime;(g) wherein the 1- or 10- nitrogen atom of R bears a phenyl or substituted phenyl substituent, which comprises reacting the corresponding amine with a benzyne;(h) wherein the 1- or 10- nitrogen atom of R is monoor di- substituted by an aliphatic, cycloaliphatic or araliphatic group, which comprises reacting a corresponding primary or secondary amine with a compound of the formula R5X where R5 is an aliphatic, cyclaliphatic or araliphatic group and X is a readily eliminatable group;(i) wherein the 1- or 10- nitrogen atom of R forms part of a hydroxy-substituted heterocyclic ring which contains at least 3 carbon atoms, which comprise cyclisation of a compound as defined above in which the nitrogen of R is substituted by a hydroxyalkyl group carrying an eliminatable group, there being at least three carbon atoms between the nitrogen atom of the amino group and the readily eliminatable gro?p;(j) wherein R is an aminomethyl group in which the methyl group is substituted, which comprises reducing the corresponding substituted nitromethyl compound;(k) wherein the 1- or 10- nitrogen atom of R is substituted by an aminoacyl group (the amino group of which unsubstituted, or substituted by one or two alkyl groups, which comprises reacting a corresponding haloacyl compound with ammonia or a monoor dialkylamine;(1) wherein the 1- or 10- nitrogen atom of R forms part of a heterocyclic ring, which comprises reacting the corresponding unsubstituted amine with a compound XR7X where X is a readily eliminatable group and R7 is a divalent alkylene group (which may be interrupted by O or S) or a cyclic group bearing two monovalent alkylene groups; or(m) wherein the 1- or 10- nitrogen atom or R is substituted by an aliphatic or araliphatic group, which comprises reducing the corresponding compound in which the said nitrogen atom is linked to said group by a double bond. The products have been found to possess antiviral activity. This invention relates to a process for the preparation of 7,7dimethyl-¢2,2,1!-bicycloheptanes having at the 1-positions a group R, and the physiologically acceptable salts thereof, wherein R is an amino or aminomethyl group possessing a basic nitrogen atom and is substituted at the amino nitrogen atom (via a single or double bond) and/or at the 10- carbon atom by one or more C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl groups, which may be unsubstituted or substituted by an amino, mono or dialkylamino,imino, hydroxy, thiol, an esterified or etherified hydroxy or thiol group or (when a basic nitrogen atom is also present on the group) an oxo group in an .alpha.-position in relation to the R nitrogen atom; a C3-8 cyclo-alkyl group; a monocyclic aralkyl, aralkenyl or aralkynyl group; a phenyl group or substituted phenyl group; a 5 or 6 membered heterocyclic aryl group; or wherein the nitrogen atom of R forms part of 4 to 8 membered heterocyclic ring which may be unsubstituted or substituted by a C1-6 alkyl, hydroxy or C3-10 cycloalkyl group or which may be fused to a benzene ring;(a) wherein the group R possesses a methylene group in an .alpha.-position in relation to the 1- or 10- nitrogen atom, which comprises reducing the corresponding amide;(b) wherein R is a methylamino group, which comprises reducing an ??ter of the corresponding carboxyamino compound; (c) wherein R is a methylamino group, which comprises reductively methylating the corresponding primary amine;(d) wherein the 1- or 10- nitrogen atom of R is linked by a double bond to an aliphatic or araliphatic substituent, which comprises condensing the corresponding primary amine with an aldehyde or ketone;(e) wherein the product is 1,3,5-tris-(bornan-10-yl)-1,3,5-hexahydrotriazine, which comprises reacting 10bornanamine with formaldehyde;(f) wherein R is an aminomethyl group in which one of the hydrogen atoms on the methyl carbon atom is substituted, which comprises reducing the corresponding ketoxime;(g) wherein the 1- or 10- nitrogen atom of R bears a phenyl or substituted phenyl substituent, which comprises reacting the corresponding amine with a benzyne;(h) wherein the 1- or 10- nitrogen atom of R is monoor di- substituted by an aliphatic, cycloaliphatic or araliphatic group, which comprises reacting a corresponding primary or secondary amine with a compound of the formula R5X where R5 is an aliphatic, cyclaliphatic or araliphatic group and X is a readily eliminatable group;(i) wherein the 1- or 10- nitrogen atom of R forms part of a hydroxy-substituted heterocyclic ring which contains at least 3 carbon atoms, which comprise cyclisation of a compound as defined above in which the nitrogen of R is substituted by a hydroxyalkyl group carrying an eliminatable group, there being at least three carbon atoms between the nitrogen atom of the amino group and the readily eliminatable gro?p;(j) wherein R is an aminomethyl group in which the methyl group is substituted, which comprises reducing the corresponding substituted nitromethyl compound;(k) wherein the 1- or 10- nitrogen atom of R is substituted by an aminoacyl group (the amino group of which unsubstituted, or substituted by one or two alkyl groups, which comprises reacting a corresponding haloacyl compound with ammonia or a monoor dialkylamine;(1) wherein the 1- or 10- nitrogen atom of R forms part of a heterocyclic ring, which comprises reacting the corresponding unsubstituted amine with a compound XR7X where X is a readily eliminatable group and R7 is a divalent alkylene group (which may be interrupted by O or S) or a cyclic group bearing two monovalent alkylene groups; or(m) wherein the 1- or 10- nitrogen atom or R is substituted by an aliphatic or araliphatic group, which comprises reducing the corresponding compound in which the said nitrogen atom is linked to said group by a double bond. The products have been found to possess antiviral activity. [CA1064928A]
IE46174A 1973-03-06 1974-03-05 10-bornanamine and 7,7-dimethylnorbornan-1-amine and derivatives IE39712B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1089573 1973-03-06
GB1089473A GB1468349A (en) 1973-03-06 1973-03-06 10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereof

Publications (2)

Publication Number Publication Date
IE39712L IE39712L (en) 1974-09-06
IE39712B1 true IE39712B1 (en) 1978-12-20

Family

ID=26247839

Family Applications (1)

Application Number Title Priority Date Filing Date
IE46174A IE39712B1 (en) 1973-03-06 1974-03-05 10-bornanamine and 7,7-dimethylnorbornan-1-amine and derivatives

Country Status (9)

Country Link
JP (1) JPS5029547A (en)
AT (1) AT353247B (en)
CA (1) CA1064928A (en)
CH (1) CH616646A5 (en)
DE (1) DE2410492A1 (en)
FR (1) FR2220260B1 (en)
IE (1) IE39712B1 (en)
LU (1) LU69557A1 (en)
NL (1) NL7402940A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000051547A2 (en) * 1999-03-03 2000-09-08 Merck & Co., Inc. Inhibitors of prenyl-protein transferase

Also Published As

Publication number Publication date
CA1064928A (en) 1979-10-23
FR2220260A1 (en) 1974-10-04
AT353247B (en) 1979-11-12
FR2220260B1 (en) 1977-03-11
CH616646A5 (en) 1980-04-15
NL7402940A (en) 1974-09-10
IE39712L (en) 1974-09-06
JPS5029547A (en) 1975-03-25
AU6628074A (en) 1975-09-11
LU69557A1 (en) 1974-06-21
DE2410492A1 (en) 1974-09-26
ATA179774A (en) 1979-04-15

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