GB750925A - Improvements in and relating to pyridine derivatives and the manufacture thereof - Google Patents

Improvements in and relating to pyridine derivatives and the manufacture thereof

Info

Publication number
GB750925A
GB750925A GB2948753A GB2948753A GB750925A GB 750925 A GB750925 A GB 750925A GB 2948753 A GB2948753 A GB 2948753A GB 2948753 A GB2948753 A GB 2948753A GB 750925 A GB750925 A GB 750925A
Authority
GB
United Kingdom
Prior art keywords
nitropyridine
hydroxy
amino
prepared
converted
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
GB2948753A
Inventor
Frederick Charles Copp
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
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB2948753A priority Critical patent/GB750925A/en
Publication of GB750925A publication Critical patent/GB750925A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises substituted pyridines of the general formula <FORM:0750925/IV(a)/1> wherein R1 represents a straight-chain alkyl or hydroxyalkyl group having from 1 to 3 carbon atoms and R2 represents a group of the formula -(CH2)nNR3R4 or <FORM:0750925/IV(a)/2> n being 2, 3 or 4, and R3 and R4 represent the same or different alkyl groups which contain from 1 to 3 carbon atoms, or R3 and R4 together with the nitrogen atom form the 1-pyrrolidinyl or piperidino group, and acid addition salts thereof, and the preparation thereof by heating a 2-halogeno-5-nitropyridine with an amine of the formula NHR1R2, wherein R1 and R2 have the above significance, e.g. in a solvent such as ethanol. The reaction may be carried out in the presence of an acid binding agent, e.g. sodium acetate. An alternative method claimed for the preparation of compounds of the above general formula in which R2 represents the <FORM:0750925/IV(a)/3> group is by reacting 2-halogeno-5-nitropyridine with a substituted phenol of the formula <FORM:0750925/IV(a)/4> and reacting the resulting product of the formula <FORM:0750925/IV(a)/5> with formaldehyde and an amine of the formula NHR3R4 wherein R3 and R4 have the above significance. Suitable salts mentioned are the hydrochloride, acid oxalate and embonate salts. In Example 1, 2-[N-(b -hydroxyethyl)-N-(b - piperidinoethyl) amino] - 5 - nitropyridine is prepared by heating b -piperidinoethylamine and ethylene oxide in a closed vessel to form b - (b - piperidinoethylamino) - ethanol which is then reacted with 2-chloro-5-nitropyridine, and is converted to the hydrochloride salt. By a similar procedure the following compounds are prepared:-b - (b - diethylaminoethylamino) - ethanol which forms 2-[N-(b -diethylaminoethyl)-N - (b - hydroxyethyl) - amino] - 5 - nitropyridine and the acid oxalate thereof; b -(g -methylisopropylaminopropylamino) - ethanol which forms 2 - [N - (b - hydroxyethyl) - N - (g - methylisopropylaminopropyl) - amino] - 5 - nitropyridine and the acid oxalate thereof; b - (g - 1 - pyrrolidinylpropylamino) - ethanol which forms 2-[N-(b -hydroxyethyl)-N-(g -1-pyrrolidinylpropyl) - amino] - 5 - nitropyridine and the acid oxalate thereof; b -(g -piperidinopropylamino)-ethanol which forms 2-[N-(b -hydroxyethyl) - N - (g - piperidinopropyl) - amino] - 5 - nitropyridine and the acid oxalate thereof; b - (g - dipropylaminopropylamino) - ethanol which forms 2 - [N - (g - dipropylaminopropyl)-N - (b - hydroxyethyl) - amino] - 5 - nitropyridine and the acid oxalate thereof; b -(d -piperidinobutylamino)-ethanol which forms 2-[N-(b -hydroxyethyl) - N - (d - piperidinobutyl) - amino] - 5 - nitropyridine and the acid oxalate thereof. In Example 2, 2-[N-(g -hydroxypropyl) - N - (g - 1 - pyrrolidinylpropyl)-amino]-5-nitropyridine is prepared by heatin g -1-pyrrolidinylpropylamine and g -chloropropanol to form g -(g -1-pyrrolidinylpropylamino) propanol which is then reacted with 2-chloro-5-nitropyridine, and may be converted into the acid oxalate salt. In Example 3, 2-[N-ethyl-N-(g - 1 - pyrrolidinylpropyl) - amino] - 5 - nitropyridine is prepared by reacting g -1-pyrrolidinylpropanol with hydrobromic acid and the resulting substituted propyl bromide is reacted with ethylamine by heating in an autoclave to form N - (g - 1 - pyrrolidinylpropyl) ethylamine which is then reacted with 2-chloro-5-nitropyridine, and may be converted into the hydrochloride salt. By a similar procedure the following compounds are prepared:-N-(g -piperidinopropyl) methylamine which forms 2 - [N - methyl - N - (g piperidinopropyl)-amino]-5-nitropyridine and the acid oxalate thereof; N - (g - piperidinopropyl) ethylamine which forms 2 - [N - ethyl - N - (g - piperidinopropyl) amino] - 5 - nitropyridine and the acid oxalate, and embonate salts thereof; N-(g -isopropylpropylaminopropyl) ethylamine which forms 2 - [N - ethyl - N - (g - isopropylpropylaminopropyl) amino]-5-nitropyridine and the acid oxalate salt thereof. In Example 4, 2-[(4-hydroxy - 3 - piperidinomethyl) - N - methylanilino] - 5 - nitropyridine is prepared by heating 4 - hydroxy - N - methylacetanilide, formalin and piperidine to form 4-hydroxy-3-piperidinomethyl - N - methylacetanilide which is converted to the hydrochloride salt, treated with concentrated hydrochloric acid to form 4 - methylamino - 2 - piperidinomethylphenol dihydrochloride which is reacted with 2-chloro-5-nitropyridine in the presence of sodium acetate and potassium carbonate, and is converted to the hydrochloride salt. By a similar procedure the following compounds are prepared: 3-diethylaminomethyl - 4 - hydroxy - N - methylacetanilide hydrochloride, 2 - diethylaminomethyl - 4 - methylaminophenol dihydrochloride and 2-[(3 - diethylaminomethyl - 4 - hydroxy) - N - methylanilino] - 5 - nitropyridine and the hydrochloride salt thereof. In Example 5, 2-[(3 - diethylaminomethyl - 4 - hydroxy) - N - methylanilino] - 5 - nitropyridine is prepared by reacting 2 - chloro - 5 - nitropyridine and 4-methylaminophenol in the presence of sodium acetate to form 2-(41-hydroxy-N-methylanilino)-5-nitropyridine which is then heated with paraformaldehyde, diethylamine, and is converted to the hydrochloride salt. By a similar procedure 2 - [(4 - hydroxy - 3 - 11 - pyrrolidinylmethyl) - N - methylanilino] - 5 - nitropyridine is prepared from 2-(41-hydroxy-N-methylanilino)-5-nitropyridine, paraformaldehyde and pyrrolidine and is converted to the hydrochloride salt; 2 - [(4 - hydroxy - 3 - piperidinomethyl) - N - ethylanilino] - 5 - nitropyridine is prepared from 2 - (41 - hydroxy - N - ethylanilino) - 5 - nitropyridine (obtained by reacting 4-ethylaminophenol and 2-chloro-5-nitropyridine), piperidine and paraformaldehyde, and is converted to the hydrochloride and embonate salts; 2 - [(4 - hydroxy - 3 - piperidinomethyl) - N - propylanilino] - 5 - nitropyridine is prepared from 2 - (41 - hydroxy - N - propylanilino) - 5 - nitropyridine (obtained by reacting 4-propylaminophenol and 2 - chloro - 5 - nitropyridine), piperidine and paraformaldehyde, and is converted to the acid oxalate salt.
GB2948753A 1953-10-26 1953-10-26 Improvements in and relating to pyridine derivatives and the manufacture thereof Expired GB750925A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2948753A GB750925A (en) 1953-10-26 1953-10-26 Improvements in and relating to pyridine derivatives and the manufacture thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2948753A GB750925A (en) 1953-10-26 1953-10-26 Improvements in and relating to pyridine derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB750925A true GB750925A (en) 1956-06-20

Family

ID=10292322

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2948753A Expired GB750925A (en) 1953-10-26 1953-10-26 Improvements in and relating to pyridine derivatives and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB750925A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0114878A1 (en) * 1982-07-26 1984-08-08 American Hospital Supply Corp Phthalazine substituted aminomethyl benzene derivatives, compositions and use.
US4567272A (en) * 1983-09-21 1986-01-28 Rutgerswerke Aktiengesellschaft Pyrrole containing 2-aminonitropyridine derivatives
EP0424848A2 (en) * 1989-10-24 1991-05-02 Hoechst-Roussel Pharmaceuticals Incorporated Aminopyridinylaminophenols and related compounds, a process and intermediates for their preparation and their use as medicaments
WO1998028257A1 (en) * 1996-12-24 1998-07-02 Chugai Seiyaku Kabushiki Kaisha Aromatic amine derivatives having nos inhibitory effect

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0114878A1 (en) * 1982-07-26 1984-08-08 American Hospital Supply Corp Phthalazine substituted aminomethyl benzene derivatives, compositions and use.
EP0114878A4 (en) * 1982-07-26 1986-03-18 American Hospital Supply Corp Phthalazine substituted aminomethyl benzene derivatives, compositions and use.
EP0310155A1 (en) * 1982-07-26 1989-04-05 The Du Pont Merck Pharmaceutical Company Heteroaryl substituted aminomethyl benzene derivatives, compositions and use
US4567272A (en) * 1983-09-21 1986-01-28 Rutgerswerke Aktiengesellschaft Pyrrole containing 2-aminonitropyridine derivatives
EP0424848A2 (en) * 1989-10-24 1991-05-02 Hoechst-Roussel Pharmaceuticals Incorporated Aminopyridinylaminophenols and related compounds, a process and intermediates for their preparation and their use as medicaments
EP0424848A3 (en) * 1989-10-24 1991-10-02 Hoechst-Roussel Pharmaceuticals Incorporated Aminopyridinylaminophenols and related compounds, a process and intermediates for their preparation and their use as medicaments
WO1998028257A1 (en) * 1996-12-24 1998-07-02 Chugai Seiyaku Kabushiki Kaisha Aromatic amine derivatives having nos inhibitory effect

Similar Documents

Publication Publication Date Title
US2948736A (en) New anilides and process for their production
GB750925A (en) Improvements in and relating to pyridine derivatives and the manufacture thereof
GB828393A (en) New phenthiazine derivatives and processes for their preparation
CA1191158A (en) Nitrobenzoic acid amide derivatives
US2579478A (en) Heterocyclic compounds
GB666457A (en) Carbonyl chlorides and monocarboxyamides of piperazine and process for the preparation thereof
KR970701177A (en) Acetate Amide Derivatives and Methods for Making the Same (AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF)
ES423058A1 (en) 3-(isopropyl amino alkoxy)-2-phenyl-isoindolin-1-ones
US2490780A (en) Para-aminobenzamides, acid addition salts thereof, and their production
GB634073A (en) Process for the preparation of local anaesthetics
US2647900A (en) 9-(2, 3-dihydroxypropylaminoethylamino)-acridines and their preparation
GB651596A (en) Manufacture of n-(2-pyridyl)-n-(p-chloro-benzyl)-n:n-dimethyl-ethylenediamine
GB690274A (en) Antihistaminic substances
GB757704A (en) Improvements in amino derivatives of n-alkyl substituted aspartic acids and their functional derivatives
KR790001498B1 (en) Process for the preparation of isoquinolin derivatives
GB744281A (en) Improvements in and relating to pyridine derivatives and the manufacture thereof
US3413111A (en) Manufacture of herbicidal materials
US2677697A (en) Basic derivatives of substituted cinnamic acids and methods of preparing same
GB582535A (en) Manufacture of basic esters and basic amides of 1-phenyl-cycloalkyl-1-carboxylic acids, and the quaternary ammonium compounds thereof
US2615895A (en) Sxyxcooh
IE43092B1 (en) A new aminating process
GB802725A (en) Improvements in or relating to phenthiazine derivatives and processes for their production
US1936547A (en) Nitrogen containing compounds of the pyridine and quinoline series
GB835802A (en) Process for the production of new anilides and salts thereof
GB640365A (en) Improvements in or relating to the preparation of new quinoline derivatives