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IE33576L - N, n'-alkylene bis (benzamides) - Google Patents

N, n'-alkylene bis (benzamides)

Info

Publication number
IE33576L
IE33576L IE691220A IE122069A IE33576L IE 33576 L IE33576 L IE 33576L IE 691220 A IE691220 A IE 691220A IE 122069 A IE122069 A IE 122069A IE 33576 L IE33576 L IE 33576L
Authority
IE
Ireland
Prior art keywords
alkyl
bis
acid
alkylene
compounds
Prior art date
Application number
IE691220A
Other versions
IE33576B1 (en
Original Assignee
Sterling Drug 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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of IE33576L publication Critical patent/IE33576L/en
Publication of IE33576B1 publication Critical patent/IE33576B1/en

Links

Classifications

    • 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
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/42—Y being a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Indole Compounds (AREA)

Abstract

1,257,199. N,N<SP>1</SP>-Alkylene bis-(benzamides). STERLING DRUG Inc. 14 Aug., 1969 [30 Aug., 1968], No. 40793/69. Heading C2C. Novel N,N<SP>1</SP>-alkylene bis-(benzamides) of the formulµ and where Q is C 1-6 alkyl, C 3-6 alkoxyalkyl, C 3-6 alkenyl, halo-C 1-6 alkyl, halo-C 2-6 alkenyl, C 3-6 cycloalkyl phenyl or BN-(C 1-6 alkyl), where BN is di-(C 1-6 alkyl) amino or a 5-7 membered saturated nitrogen containing monocyclic heterocyclic ring, R is H or C 1-6 alkyl, Y is C 5-12 alkylene, having at least 5 carbon atoms between its 2 connecting linkages, wherein a carbon atom of said alkylene more than 2 carbon atoms removed from the amide N atoms can be replaced by -O-, -S-, -S-S-, -Se- Se-, =SO, =SO 2 , =NH, =N-(C 1-6 alkyl), =N-(CO-phenyl-4-10-Q),=C=O, -CH = CH- or -C#C-, or Y is Y<SP>1</SP>-Z-Y<SP>11</SP>, where Y<SP>1</SP> is C 1-4 alkylene, Y<SP>11</SP> is a direct linkage ; or C 1-4 alkylene, Z is phenyl or C 3-6 cycloalkyl, and 'the benzene ring of the phenyl radical of Formula I is, if desired, further substituted by, for example, C 1-6 alkyl, C 1-6 alkoxy, halogen, benzyloxy or OH are prepared by reacting an amine of the formula RNH-Y-NHR with at least two molar equivalents of the appropriate benzoylating agents. In addition, compounds, formula I, in which the phenyl radical is substituted by OH may be obtained by hydrogenolysis of the corresponding benzyloxy substituted compounds, compounds in which Q is di-(C 1-6 alkyl) amino (C 1-6 alkyl) by reacting the corresponding compounds in which Q is OH with the appropriate di-.(C 1-6 alkyl) amino-(C 1-6 alkyl) halides, and compounds, in which the alkylene chain Y is interrupted by = C = 0, by hydrolysing the corresponding ethylene ketals. In comparative examples, N,N<SP>1</SP> - heptamethylene bis - (3 - methoxybenzamide, N,N<SP>1</SP>- heptamethylene bis (2 - methoxybenzamide), N,N<SP>1</SP> - heptamethylene bis - (4 - methylthiobenzamide) and N,N<SP>1</SP>-hexamethylene bis-(4-hydroxybenzamide) are made by reacting the appropriate amines with the corresponding acid chlorides or esters. N,N<SP>1</SP> - Heptamethylene bis - (4 - hydroxybenzamide) is obtained by hydrolysing N,N<SP>1</SP> - heptamethylene bis-(4-acetoxybenzamide) which is made by reacting 1,7-heptanediamine with 4-acetoxybenzoyl chloride. The following intermediates are also prepared: 4-trideuteromethoxy benzoic acid, acid chloride and ethyl ester thereof, 4-ethoxybenzoyl chloride, 4-acetoxybenzoic acid and acid chloride, 4 - (2,2,2 - trifluoroethoxy) benzoic acid, acid chloride and ethyl ester, 4-(2,2-dichlorovinyloxy) benzoic acid, acid chloride and ester, 4-allyloxybenzoic acid, acid chloride and ester, 3,5- dibenzyloxy - 4 - methoxy -benzoic acid, acid chloride and methyl ester, 4-pentadeuteroethoxybenzoic acid, acid chloride and ethyl ester, 2,8-nonanediamine, ethylene ketal of 1,4 - diamino - 4-heptanone, ethylene ketal of N,N<SP>1</SP> - (4 - oxoheptamethylene) bis - (phthalimide), 1,1,5 - trimethyl -1,7 - heptanediamine, N 1 - acetyl - 1,1,5 - trimethyl - 1,7 - heptanediamine, N,N<SP>1</SP> - dimethyl 1,7 - heptanediamine, N,N<SP>1</SP> - dibenzal - 1,7 - heptanediamine, and the dimethiodide thereof, 3-heptyne-1,7- diamine, 7 - chloro - 3 - heptyne - 1 - ol, 7-chloro- 3-heptyne-1-yl-4-toluene sulphonate, N,N<SP>1</SP>- (3 - heptyne-1,7 - diyl) bis - phthalimide, 1,4,7- heptane - triamine, N,N<SP>1</SP>N<SP>11</SP> - (1,4,7 - heptamethylene) tris - phthalamide, and 4 - (2- methoxyethoxy) benzoic acid Pharmaceutical compositions, suitable for oral or parenteral administration and having adrenal hypertrophy, antifertility and hypocholestremic activities, contain the above novel compounds and conventional pharmaceutically acceptable carriers. [GB1257199A]
IE1220/69A 1968-08-30 1969-08-29 Chemical compounds and their preparation IE33576B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US75637368A 1968-08-30 1968-08-30

Publications (2)

Publication Number Publication Date
IE33576L true IE33576L (en) 1970-02-28
IE33576B1 IE33576B1 (en) 1974-08-21

Family

ID=25043187

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1220/69A IE33576B1 (en) 1968-08-30 1969-08-29 Chemical compounds and their preparation

Country Status (12)

Country Link
JP (1) JPS505181B1 (en)
AT (1) AT299162B (en)
BE (1) BE738084A (en)
BR (1) BR6911910D0 (en)
CH (1) CH511803A (en)
DE (1) DE1943787A1 (en)
ES (1) ES370985A1 (en)
FR (1) FR2016691B1 (en)
GB (1) GB1257199A (en)
IE (1) IE33576B1 (en)
IL (1) IL32881A (en)
NL (1) NL6913186A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53105616U (en) * 1977-01-27 1978-08-25
JPS55144771U (en) * 1979-04-05 1980-10-17
US20230416181A1 (en) * 2020-12-18 2023-12-28 Dow Global Technologies Llc Oxygenated solvent odorant removal composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1320717A (en) * 1959-10-08 1963-03-15 Sterling Drug Inc Process for the preparation of n, n'-di - [(halogenated lower alkanoyl)] aliphatic diamine derivatives

Also Published As

Publication number Publication date
NL6913186A (en) 1970-03-03
FR2016691B1 (en) 1974-04-12
FR2016691A1 (en) 1970-05-08
BR6911910D0 (en) 1973-01-04
IL32881A (en) 1974-03-14
JPS505181B1 (en) 1975-02-28
CH511803A (en) 1971-08-31
IL32881A0 (en) 1969-12-31
AT299162B (en) 1972-06-12
GB1257199A (en) 1971-12-15
ES370985A1 (en) 1971-08-01
DE1943787A1 (en) 1970-03-05
BE738084A (en) 1970-03-02
IE33576B1 (en) 1974-08-21

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