GB924961A - Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof - Google Patents

Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof

Info

Publication number
GB924961A
GB924961A GB8878/59A GB887859A GB924961A GB 924961 A GB924961 A GB 924961A GB 8878/59 A GB8878/59 A GB 8878/59A GB 887859 A GB887859 A GB 887859A GB 924961 A GB924961 A GB 924961A
Authority
GB
United Kingdom
Prior art keywords
alkyl
alkoxy
phenyl ring
compounds
benzyl
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
GB8878/59A
Inventor
Frederick Charles Copp
Geoffrey George Coker
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 to FR837356A priority Critical patent/FR558M/fr
Priority to BE588558D priority patent/BE588558A/xx
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB8878/59A priority patent/GB924961A/en
Priority to ES0256264A priority patent/ES256264A1/en
Priority to GR600129331A priority patent/GR29331B/en
Priority to CH1658665A priority patent/CH436259A/en
Priority to CH270760A priority patent/CH422758A/en
Priority to LU38374D priority patent/LU38374A1/xx
Priority to FR821114A priority patent/FR1421206A/en
Priority to NL249341A priority patent/NL129619C/xx
Priority to DK97360A priority patent/DK104353C/en
Priority to DE1960W0027453 priority patent/DE1238485C2/en
Publication of GB924961A publication Critical patent/GB924961A/en
Priority to NL6909922A priority patent/NL6909922A/xx
Expired legal-status Critical Current

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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
    • A41D27/00—Details of garments or of their making
    • A41D27/02—Linings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
    • C07D333/28—Halogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

The invention comprises quaternary amino compounds containing a cation of the formula R.W.CH2CH2.N+XY.CH2.L, wherein R is a phenyl ring, substituted in the m- or p-positions by a halogen, alkyl, alkoxy, hydroxy, formyl, acetyl, alkoxycarbonyl, amino, acetamido, cyano or nitro substituent when L is a phenyl ring optionally bearing a halogen, alkyl, alkoxy, cyano or nitro substituent or a thienyl or furyl ring optionally bearing a 5-halo or 5-nitro substituent; or R is a phenyl ring optionally substituted in the o-position by a halogen, alkyl, alkoxy, hydroxy, formyl, acetyl, alkoxy-carbonyl, amino, acetamido, cyano or nitro substituent when L is a phenyl ring substituted in the m- or p-position by a halogen, alkyl, alkoxy cyano or nitro substituent; W is a straight saturated chain containing 1-3 nonadjacent oxygen atoms and 0-16 carbon atoms and X and Y are each an alkyl or alkyl group or NXY forms a pyrrolidino, piperidino or morpholino ring, the terms "alkyl", "alkoxy" and "alkoxycarbonyl" denoting groups of 1-4 carbon atoms; with the exception of compounds containing a N-5-p-chlorophenoxy-3-oxapentyl-N-p-chlorobenzyl-N, N-dimethylammonium, N - p - t - butylphenoxyethoxyethyl-N-benzyl-N,N-dimethylammonium, N - benzyl-N-5-p-methylphenoxy-3-oxapentyl-N,N-dimethylammonium, N - benzyl - N,N-diethyl - N-2-m-methoxyphenoxyethylammonium or N - benzyl - N, N - diethyl - N - 2 - m butoxyethylammonium cation. It comprises also a process for preparing these compounds by reacting the corresponding tertiary amine with a reactive ester of the hydroxy derivative of the group it is desired to introduce, e.g. with an alkylating agent. Alternatively a secondary amine may be treated with two equivalents of an alkylating agent or with an a ,o -disubstituted butane, pentane or 3-oxapentane (to form the pyrrolidine, piperidine or morpholine groups). Similarly the products may also be made by internal quaternisation of a tertiary amine R.W.CH2CH2.N(XYZ). CH2L wherein XY is a tetramethylene pentamethylene or 3-oxapentamethylene chain bearing a terminal ester group Z. When R is a phenyl ring bearing an amino substituent it is necessary to protect the amine group with an acyl, alkoxycarbonyl or hydrocarbonsulphonyl group which is subsequently removed by hydrolysis of the quaternary compound. Salts of the products are made by conventional processes of salt - formation, double decomposition and anion exchange. Secondary and tertiary amines, corresponding to the above quaternary compounds, are prepared by standard methods. p-2-Bromoethoxyacetophenone is made by the action of ethylene dibromide on p-hydroxyacetophenone Phenoxy alkyl halides of the formula R2-C6H4.W.CH2CH2Z, wherein R2 is Br, CH3, CH3O or NO2 and Z is Br or Cl are described. 1-o-Bromobenzyloxy-2-chloroethane is made by reacting o-bromobenzyl bromide with ethylene glycol and chlorinating the resulting 1-o-bromobenzyloxy-2-hydroxyethane. Pharmaceutical preparations for the treatment of nematode infestations comprise the above quaternary compounds (including the compounds specifically excluded from the product claims), suitably in the form of salts with borofluoride, perchlorate, laurylsulphate, dodecylsulphonate, p-toluenesulphonate, p-chlorobenzenesulphonate, p-bromobenzenesulphonate, p-acylaminobenzenesulphonate, acylaminocarboxylate, diphenylsulphonate, naphthalene mono- and di-sulphonate, naphthoate, dihydroxydiarylmethane dicarboxylate, piperazine-1,4-bis-carbodithioate, diaminostilbenedisulphonate, phenate or trichlorophenate anions, and a pharmaceutical carrier. The preparations may suitably take the form of tablets, granules, capsules, cachets, suspensions, emulsions or a draft or drench in water or a syrup.
GB8878/59A 1959-03-13 1959-03-13 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof Expired GB924961A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
FR837356A FR558M (en) 1959-03-13
BE588558D BE588558A (en) 1959-03-13
GB8878/59A GB924961A (en) 1959-03-13 1959-03-13 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof
ES0256264A ES256264A1 (en) 1959-03-13 1960-03-04 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof
GR600129331A GR29331B (en) 1959-03-13 1960-03-08 METHOD OF PREPARATION OF QUARTERLY AMMONIA COMPOUNDS.
CH1658665A CH436259A (en) 1959-03-13 1960-03-10 Process for the production of quaternary ammonium compounds
CH270760A CH422758A (en) 1959-03-13 1960-03-10 Process for the production of new quaternary ammonium compounds
LU38374D LU38374A1 (en) 1959-03-13 1960-03-11
FR821114A FR1421206A (en) 1959-03-13 1960-03-11 Quaternary ammonium compounds, in particular bearing an optionally substituted phenoxyethyl group, and their preparation
NL249341A NL129619C (en) 1959-03-13 1960-03-11
DK97360A DK104353C (en) 1959-03-13 1960-03-12 Process for the preparation of quaternary ammonium compounds.
DE1960W0027453 DE1238485C2 (en) 1959-03-13 1960-03-14 Process for the preparation of quaternary ammonium salts
NL6909922A NL6909922A (en) 1959-03-13 1969-06-27

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8878/59A GB924961A (en) 1959-03-13 1959-03-13 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof
GB887959 1959-03-13
GB3955959 1959-11-20
GB3955859 1959-11-20

Publications (1)

Publication Number Publication Date
GB924961A true GB924961A (en) 1963-05-01

Family

ID=27447685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8878/59A Expired GB924961A (en) 1959-03-13 1959-03-13 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof

Country Status (10)

Country Link
BE (1) BE588558A (en)
CH (2) CH436259A (en)
DE (1) DE1238485C2 (en)
DK (1) DK104353C (en)
ES (1) ES256264A1 (en)
FR (2) FR1421206A (en)
GB (1) GB924961A (en)
GR (1) GR29331B (en)
LU (1) LU38374A1 (en)
NL (2) NL129619C (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49101519A (en) * 1973-01-18 1974-09-25
US3956369A (en) * 1973-05-18 1976-05-11 Ozeretskovskaya Natalia Nikola N-β-(2-acetyl-4-chlorophenoxy)-ethyl-N,N-dimethyl-N-benzyl-ammonium-p-chlorobenzene sulphonate, method for preparing same and medicinal preparation based thereon
EP0103252A2 (en) * 1982-09-11 1984-03-21 BASF Aktiengesellschaft Aryloxyalkyl amines, process for their preparation and their use in combating unwanted plant growth
WO1995011238A1 (en) * 1993-10-22 1995-04-27 Smithkline Beecham Plc Heterocyclic amines for treating ischaemic strokes
WO1995011240A1 (en) * 1993-10-22 1995-04-27 Smithkline Beecham Plc Amine derivatives as calcium channel antagonists
EP0978512A1 (en) * 1998-07-29 2000-02-09 Societe Civile Bioprojet Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications
EP0982300A2 (en) * 1998-07-29 2000-03-01 Societe Civile Bioprojet Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications
US7256312B2 (en) 2002-08-01 2007-08-14 Basf Aktiengesellschaft Method for producing aminoalkoxy benzylamines and aminoalkoxy benzonitriles as intermediates
WO2012040133A3 (en) * 2010-09-21 2012-05-10 Ge Healthcare Limited Novel precursors of radiolabelled choline analog compounds
EP4118070A4 (en) * 2020-03-11 2024-04-10 Nocion Therapeutics Inc Charged ion channel blockers and methods for use

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53144554A (en) * 1977-04-12 1978-12-15 Nattermann A & Cie New basic paraabenzoylether
DE2913523A1 (en) 1979-04-04 1980-10-23 Basf Ag SUBSTITUTED ALKYLAMONIUM SALTS, THEIR PRODUCTION AND USE FOR REGULATING PLANT GROWTH

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1117600B (en) * 1956-03-29 1961-11-23 Wellcome Found Process for the preparation of quaternary ammonium salts effective against nematodes

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49101519A (en) * 1973-01-18 1974-09-25
US3956369A (en) * 1973-05-18 1976-05-11 Ozeretskovskaya Natalia Nikola N-β-(2-acetyl-4-chlorophenoxy)-ethyl-N,N-dimethyl-N-benzyl-ammonium-p-chlorobenzene sulphonate, method for preparing same and medicinal preparation based thereon
EP0103252A2 (en) * 1982-09-11 1984-03-21 BASF Aktiengesellschaft Aryloxyalkyl amines, process for their preparation and their use in combating unwanted plant growth
EP0103252A3 (en) * 1982-09-11 1984-10-03 BASF Aktiengesellschaft Aryloxyalkyl amines, process for their preparation and their use in combating unwanted plant growth
WO1995011238A1 (en) * 1993-10-22 1995-04-27 Smithkline Beecham Plc Heterocyclic amines for treating ischaemic strokes
WO1995011240A1 (en) * 1993-10-22 1995-04-27 Smithkline Beecham Plc Amine derivatives as calcium channel antagonists
EP0978512A1 (en) * 1998-07-29 2000-02-09 Societe Civile Bioprojet Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications
EP0982300A2 (en) * 1998-07-29 2000-03-01 Societe Civile Bioprojet Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications
EP0982300A3 (en) * 1998-07-29 2000-03-08 Societe Civile Bioprojet Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications
EP2000462A3 (en) * 1998-07-29 2011-05-04 Bioprojet Non-imidazole alkylamines as histamine H3-receptor ligands and their therapeutic applications
US7256312B2 (en) 2002-08-01 2007-08-14 Basf Aktiengesellschaft Method for producing aminoalkoxy benzylamines and aminoalkoxy benzonitriles as intermediates
WO2012040133A3 (en) * 2010-09-21 2012-05-10 Ge Healthcare Limited Novel precursors of radiolabelled choline analog compounds
JP2013537239A (en) * 2010-09-21 2013-09-30 ジーイー・ヘルスケア・リミテッド New precursor
EP4118070A4 (en) * 2020-03-11 2024-04-10 Nocion Therapeutics Inc Charged ion channel blockers and methods for use

Also Published As

Publication number Publication date
NL129619C (en) 1970-08-18
LU38374A1 (en) 1960-09-12
DE1238485B (en) 1967-04-13
BE588558A (en) 1960-09-12
CH436259A (en) 1967-05-31
DE1238485C2 (en) 1967-10-26
FR1421206A (en) 1965-12-17
GR29331B (en) 1965-12-29
DK104353C (en) 1966-05-09
CH422758A (en) 1966-10-31
FR558M (en) 1961-05-29
ES256264A1 (en) 1960-08-16
NL6909922A (en) 1969-10-27

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