GB788914A - Improvements in or relating to diquaternary compounds - Google Patents

Improvements in or relating to diquaternary compounds

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Publication number
GB788914A
GB788914A GB559054A GB559054A GB788914A GB 788914 A GB788914 A GB 788914A GB 559054 A GB559054 A GB 559054A GB 559054 A GB559054 A GB 559054A GB 788914 A GB788914 A GB 788914A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
diiodide
trimethylethylene
diethyl
formula
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
GB559054A
Inventor
Donald Wallace Adamson
John Evlyn Warner Billinghurst
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 GB559054A priority Critical patent/GB788914A/en
Publication of GB788914A publication Critical patent/GB788914A/en
Expired legal-status Critical Current

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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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0788914/IV (b)/1> wherein R1 and R2 are the same or different and are each a cycloalkyl group (for example a cyclohexyl group), or a phenyl group which may carry one or more substituents, said substituents being halogen atoms (for example chlorine or bromine atoms), phenyl or lower alkyl groups (having from 1 to 4 carbon atoms) or lower alkoxy groups (having from one to four carbon atoms), the total number of carbon atoms in the alkyl and/or alkoxy groups present on either of the phenyl groups not exceeding four; n is an integer from 1 to 9; +N1 is a quaternary nitrogen atom either carrying two alkyl groups having together up to five carbon atoms, preferably two or three carbon atoms, or forming part of a pyrrolidino, piperidino or morpholino ring; +N2 is a quaternary nitrogen atom carrying at least one alkyl group having from 1 to 4 carbon atoms and either carrying two further alkyl groups giving a total of up to 9 carbon atoms, preferably a total of 3 to 6 carbon atoms, or forming part of a pyrrolidino, piperidino or morpholino ring; Y is an alkylene chain having from 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms, or +N1-Y- + N2 may be a piperazine ring in which + N1 is a quaternary nitrogen atom carrying one alkyl group having up to 4 carbon atoms and +N2 is a quaternary nitrogen atom carrying two alkyl groups having a total of up to 4 carbon atoms, the total number of carbon atoms in the alkyl groups not exceeding 6; and A- is an anion of an inorganic or organic acid which may be, for example, halide or alkyl sulphate. Such compounds may be obtained by heating with a quaternizing agent the corresponding base of the formula <FORM:0788914/IV (b)/2> in which N3 is a secondary, tertiary or quaternary nitrogen atom and N4 is a primary or tertiary or quaternary nitrogen atom when N3 is a secondary or tertiary nitrogen atom or a primary or tertiary nitrogen atom when N3 is a quaternary nitrogen atom. The products (with the exception of the piperazine compounds) can also be prepared by reacting a compound of the formula Z-Y-N2-A- with a compound of the formula R1R2C(OH)CH2(CH2)nN5, where N5 is a tertiary nitrogen atom. Compounds of formula II are obtainable by reacting a halogeno ester of the formula (III) R3O2C.CH2(CH2)n.Z (where R3 may be alkyl) with a diamine of the formula HN5-Y-N4, where N5 is a nitrogen atom carrying one alkyl group having up to 4 carbon atoms, the product obtained of formula R3O2C.CH2(CH2) n.N5-Y-N4 being either reacted with excess of a compound such as R1MgZ or R1Li (to give a carbinol II in which R1 and R2 are alike) or (where R1 and R2 are different) with about two molecular proportions of Grignard reagent to give a ketone R1.CO.CH2(CH2)n.N5-Y-N4 which is then reacted with R2Li or R2MgZ. Alternatively a halogeno compound of the formula R1R2C(OH)-CH2(CH2)nZ is reacted with the diamine NH5-Y-N4. Compounds of formula II, where R1 and/or R2 are cyclohexyl, may be obtained by hydrogenation of the corresponding phenyl derivatives. If N4 is a primary nitrogen atom the nitrile of the formula R1R2C(OH)-CH2(CH2) nNR4(CH2)mCN, where R4 is an alkyl group and m is an integer from 2 to 9 (from the reaction of R1R2C(OH)CH2(CH2)nNHR4 and Z(CH2)mCN) may be reduced to the compound of formula II. Equations for similar reactions, where N3 is a secondary or quaternary nitrogen atom, respectively, are also given. Compounds of formula II can also be prepared by reaction of compounds of the formul R1R2C(OH)(CH2)-(CH2)nBr and either H2N(CH2)qNR6R7 or H2N(CH2)q+NR6R7R8A, where q is an integer from 2 to 10 and R6 and R7 are either each alkyl groups having a total of up to eight carbon atoms or NR6R7 is a pyrrolidino, piperidino or morpholino ring and R8 is an alkyl group. Compounds of formula II in which N3 is a quaternary nitrogen atom and N4 is a tertiary nitrogen atom can be prepared by reacting compounds of the formula <FORM:0788914/IV (b)/3> where X is C.OH.CH2, with compounds of the formula HNR6R7. In Example (1) N1-(3-hydroxy - 3 : 3 - diphenylporpyl) - N1 : N2 : N2 - trimethyl-piperazinium diiodide is prepared by quaternation of the corresponding base by reaction with methyl iodide. Similarly prepared are (2) N2 : N2-diethyl-N1-(3-hydroxy-3 : 3 - diphenylpropyl) - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (3) N1 - (3 - hydroxy - 3 : 3 - diphenylpropyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium-2-pyrrolidinium diiodide; (4) N1-(3-hydroxy-3 : 3 - diphenylpropyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium - 2 - piperidinium diiodide; (5) N1 - (3 - hydroxy - 3 : 3 - diphenylpropyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium - 2 - morpholinium diiodide; (6) N2 : N2 - diethyl - N1 - (4 - hydroxy - 4 : 4 - diphenylbutyl) - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (7) N2 : N2 - diethyl - N1 - (5 - hydroxy - 5 : 5 - diphenylpentyl) - N1 : N1 : N1 - trimethylethylene - 1 : 2 - diammonium diiodide; (8) N1-(6-hydroxy-6 : 6-diphenylhexyl) - N1 : N2 : N2 - trimethylpiperazinium diiodide; (9) N2 : N2-diethyl-N1-(6-hydroxy - 6 : 6 - diphenylhexyl) - N1 : N1 : N2 - trimethylethylen - 1 : 2 - diammonium diiodide; (10) N1 - (6 - hydroxy - 6 : 6 - diphenylhexyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium - 2 - piperidinium diiodide; (11) N1 - (6 - hydroxy - 6 : 6 - diphenylhexyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium-2-morpholinium diiodide; (12) N1-ethyl-N1-(6-hydroxy - 6 : 6 - diphenylhexyl) - N1 : N2 - dimethylethylene - 1 - ammonium - 2 - morpholinium diiodide; (13) N2 : N2 - di - n - butyl - N1 - (6 - hydroxy - 6 : 6 - diphenylhexyl) - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (14) N2 : N2-diethyl-N1-(7 - hydroxy - 7 : 7 - diphenylheptyl) - N1 : N1 : N2-trimethylethylene - 1 : 2 - diammonium diiodide; (15) N2 : N2-diethyl-N1-(9-hydroxy-9 : 9-diphenylnonyl) - N1 : N1 : N2 - trimethylethylene-1 : 2-diammonium diiodide; (16) N2 : N2-diethyl - N1 - (11 - hydroxy - 11 : 11 - diphenylundecyl) - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; N2 : N2 - diethyl - N1 - [3 - hydroxy - 3 : 3 - di - (4 - methylphenyl) propyl] - - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (18) N2 : N2-diethyl-N1-[5 - hydroxy - 5 - (4 - methylphenyl) - 5 - phenylpentyl] - - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (19) N2 : N2 - diethyl - N1 - [6 - hydroxy - 6 - (4 - methylphenyl) - 6 - phenylhexyl] - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (20) N2 : N2 - diethyl - N1 - [6 - hydroxy - 6 : 6 - di - (2 - methylphenyl) hexyl] - N1 : N1 : N2 - trimethylethylene-1 : 2 - diammonium diiodide; (21) N2 : N2-diethyl - N1 - [6 - hydroxy - 6 : 6 - di - (3 - methylphenyl) hexyl]- N1 : N1 : N2 - trimethylethylene-1 : 2 - diammonium diiodide; (22) N2 : N2-diethyl - N1 - [6 - hydroxy - 6 : 6 - di - (4 - methylphenyl) - hexyl] - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (23) N2 : N2 - diethyl - N1 - [6 - hydroxy - 6 : 6 - bis(2 : 5 - dimethylphenyl) hexyl] - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (24) N1 - [6 : 6 - di - (4 - tert. - butylphenyl) - 6 - hydroxyhexyl] - N2 : N2 - diethyl - N1 : N1 : N2 - trimethylethylene-1 : 2-diammonium diiodide; (25) N1 - [6 : 6 - di - (4 - chlorophenyl) - 6 - hydroxyhexyl] - N2 : N2 - diethyl - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (26) N2 : N2 - diethyl - N1 - [6 - hydroxy-6 : 6-di-(4-methoxyphenyl) hexyl]- N1 : N1 : N2-trimethylethylene-1 : 2-diammonium diiodide; (27) N1 - [3 - hydroxy - 3 - (4 - diphenyl) - 3 - phenylpropyl] - - N1 : N1 : N2 - trimethylethylene-1 - ammonium - 2 - morpholinium diiodide; (28) N2 : N2 - diethyl - N1 - (6 - cyclohexyl - 6 - hydroxy - - 6 - phenylhexyl) - N1 : N1 : N2 - trimethylethylethylene - 1 : 2 - diammonium diiodide; (29) N2 : N2-diethyl-N1-(6 : 6-dicyclohexyl - 6 - hydroxyhexyl) - - N1 : N1 : N2 - trimethylethylene - 1 : 2 - diammonium diiodide; (30) N1 - (6 : 6 - dicyclohexyl - 6 - hydroxyhexyl) - N1 : N1 : N2 - trimethylethylene - 1 - ammonium-2-morpholinium diiodide; (31) N1-(6 - hydroxy - 6 : 6 - diphenylhexyl - N2 : N2 : N2-trimethyl - trimethylene - 3 - ammonium - 1 - pyrrolidinium diiodide. Specifications 682,160 and 788,915 are referred to.
GB559054A 1954-02-25 1954-02-25 Improvements in or relating to diquaternary compounds Expired GB788914A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB559054A GB788914A (en) 1954-02-25 1954-02-25 Improvements in or relating to diquaternary compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB559054A GB788914A (en) 1954-02-25 1954-02-25 Improvements in or relating to diquaternary compounds

Publications (1)

Publication Number Publication Date
GB788914A true GB788914A (en) 1958-01-08

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GB559054A Expired GB788914A (en) 1954-02-25 1954-02-25 Improvements in or relating to diquaternary compounds

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GB (1) GB788914A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999051578A1 (en) * 1998-04-02 1999-10-14 Janssen Pharmaceutica N.V. Biocidal benzylbiphenyl derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6440440B1 (en) 1998-02-04 2002-08-27 Lieven Meerpoel Biocidal benzylbiphenyl derivatives
WO1999051578A1 (en) * 1998-04-02 1999-10-14 Janssen Pharmaceutica N.V. Biocidal benzylbiphenyl derivatives

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