GB844827A - Novel amine compounds and a process for the manufacture thereof - Google Patents

Novel amine compounds and a process for the manufacture thereof

Info

Publication number
GB844827A
GB844827A GB32489/58A GB3248958A GB844827A GB 844827 A GB844827 A GB 844827A GB 32489/58 A GB32489/58 A GB 32489/58A GB 3248958 A GB3248958 A GB 3248958A GB 844827 A GB844827 A GB 844827A
Authority
GB
United Kingdom
Prior art keywords
trimethyl
alkane
cyclohexyl
methyl
bis
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
GB32489/58A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB844827A publication Critical patent/GB844827A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

The invention comprises symmetrical quaternary compounds of the general formula: <FORM:0844827/IV(b)/1> wherein each m is 1 to zero, the radicals R are identical alkyl groups, R1 is an alkylene radical, R2 is a 2:6:6-trimethyl-cyclohexyl or 2:6:6-trimethyl cyclohexenyl-(1) radical and X is an anion such as a halide, sulphate phosphate, nitrate, benzenesulphonate, toluenesulphonate, citrate or tartrate radical and also corresponding secondary and tertiary amines, i.e. N:N1-bis [1-methyl-3-(21:61:61-trimethyl-cyclohexyl and cyclohexene-(1) yl)-propyl]-N:N1-dialkyl-alkane. a :w-diamines; N:N1-bis-[2-methyl-4-(21:61:61-trimethyl -cyclohexyl (and cyclohexen-(1)-yl))-butyl] -N:N1-dialkyl-alkane-a :o -diamines; N: N1-bis[1-methyl-3-(21:61:61-trimethyl - cyclohexyl (and cyclohexen-(1)-yl))-propyl] - alkane-a :w-diamines and N:N1-bis [2-methyl-4(21:61:61-trimethyl-cyclohexyl (andcyclohexen-(1)-yl))butyl] alkane a :o -diamines. The invention also comprises a processes for preparing the above compounds by treating a mono-tertiary amine R.CH2-CH2-CH(CH3).(CH2)mN(R)R with a a :o - dihalogeno - alkane, or by reductively condensing a carbonyl compound R2CH2CH2, CO,CH3, O, R2CH2,CH2,CH)CH3),CHO, R2,CH: CH,CO,CH3 or R2,CH2, CH:C(CH3)-,CHO with an a :o -diamino-alkane, alkylating the resulting di-secondary amine and then quaternizing the di-tertiary amine obtained. Mono-tertiary-amines of the formula R,CH2, CH2,CH(CH3),(CH2)m,N(R)R used as starting materials are made by reductively condensing beta-ionone, tetrahydro-ionone or 4[21:61:61-trimethyl - cyclohexen - (11) - yl] - 2 - methyl -2-buten-(1)-al with a primary alkylamine.ALSO:Anti-microbial preparations suitable for topical application (for example as creams, lotions or ointments) or parenteral administration in a sterile medium such as water, comprise symmetrical bis quaternary amines of the formula: <FORM:0844827/VI/1> wherein m is 1 or zero, the radicals R are identical alkyl groups, R1 is an alkylene radical and R2 is a 2:6:6-trimethyl-cyclohexyl or a 2:6:6-trimethyl-cyclohexenyl-(1) radical and X is an anion such as a halide, sulphate, phosphate, nitrate, benzenesulphonate, toluenesulphonate, citrate or tartrate radical (see Group IV(b)), in association with a carrier or diluent.
GB32489/58A 1958-04-17 1958-10-10 Novel amine compounds and a process for the manufacture thereof Expired GB844827A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US844827XA 1958-04-17 1958-04-17

Publications (1)

Publication Number Publication Date
GB844827A true GB844827A (en) 1960-08-17

Family

ID=22185235

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32489/58A Expired GB844827A (en) 1958-04-17 1958-10-10 Novel amine compounds and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB844827A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035174A (en) * 1975-10-09 1977-07-12 Merck & Co., Inc. Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines and methods for their preparation
US4049417A (en) * 1975-04-28 1977-09-20 Merck & Co., Inc. Alicyclic alkylene polyamine microorganism and algae growth inhibitors
US4058625A (en) * 1976-05-14 1977-11-15 Merck & Co., Inc. Broad spectrum antimicrobial compositions containing tris-(hydroxymethyl)aminomethane and polyamines
US4060639A (en) 1976-05-14 1977-11-29 Merck & Co., Inc. Broad spectrum antibacterial compositions containing tris-(hydroxymethyl)-aminoethane and dicycloaliphatic-alkyl polyamines
US4065497A (en) * 1976-03-30 1977-12-27 Merck & Co., Inc. Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049417A (en) * 1975-04-28 1977-09-20 Merck & Co., Inc. Alicyclic alkylene polyamine microorganism and algae growth inhibitors
US4035174A (en) * 1975-10-09 1977-07-12 Merck & Co., Inc. Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines and methods for their preparation
US4065497A (en) * 1976-03-30 1977-12-27 Merck & Co., Inc. Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines
US4058625A (en) * 1976-05-14 1977-11-15 Merck & Co., Inc. Broad spectrum antimicrobial compositions containing tris-(hydroxymethyl)aminomethane and polyamines
US4060639A (en) 1976-05-14 1977-11-29 Merck & Co., Inc. Broad spectrum antibacterial compositions containing tris-(hydroxymethyl)-aminoethane and dicycloaliphatic-alkyl polyamines

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