GB1026778A - 2-benzyl-2-imidazoline compounds and compositions including them - Google Patents

2-benzyl-2-imidazoline compounds and compositions including them

Info

Publication number
GB1026778A
GB1026778A GB10585/63A GB1058563A GB1026778A GB 1026778 A GB1026778 A GB 1026778A GB 10585/63 A GB10585/63 A GB 10585/63A GB 1058563 A GB1058563 A GB 1058563A GB 1026778 A GB1026778 A GB 1026778A
Authority
GB
United Kingdom
Prior art keywords
methyl
acid
benzyl
dimethoxy
ethylenediamine
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
GB10585/63A
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.)
Merck KGaA
Original Assignee
E Merck 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 E Merck AG filed Critical E Merck AG
Publication of GB1026778A publication Critical patent/GB1026778A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 2-benzyl-2-imidazoline compounds of the formula <FORM:1026778/C2/1> wherein R1 is methyl, R2 and R3 are independently hydrogen or methyl, and R4 is methyl whenever either or both of R2 and R3 are methyl, but otherwise is hydrogen; and acid addition salts thereof. The imidazolines may be prepared by condensing a compound of the formula <FORM:1026778/C2/2> wherein the symbols R have the meanings stated above, or a suitable functional derivative thereof (e.g. ester, ortho-ester, acid halide, amide or nitrile), with ethylenediamine or a substance or substances which yield ethylenediamine. In an Example 2,5-dimethoxy-4,6-dimethyl - benzyl cyanide is heated with ethylenediamine in the presence of carbon disulphide to form 2-(21,51-dimethoxy-41,61-dimethylbenzyl -2-imidazoline. The initial cyanide compound is obtained by chloromethylating 1,4-dimethoxy-2,6-dimethyl-benzene and reacting the substituted benzyl chloride so obtained with sodium cyanide.ALSO:Pre-shaving compositions comprise emulsions or solutions containing one or more compounds of the formula <FORM:1026778/A5-A6/1> wherein R1 is methyl, R2 and R3 are independently hydrogen or methyl, and R4 is methyl whenever either or both of R2 and R3 are methyl, but otherwise is hydrogen, or their pharmaceutically acceptable acid addition salts together with one or more of the following: alkylene diols or polyols, esters of fatty acids, alkali metal salts of fatty acids (the fatty acids in either case containing 14 to 18 carbon atoms) and polyvinylpyrrolidone. Besides polyvinylpyrrolidone, propylene glycol and isopropyl myristate are exemplified. The acid addition salts may be derived from hydrochloric, hydrobromic, sulphuric, citric or succinic acid. Mixtures of water with ethanol or isopropanol are suitable as vehicles for the compositions which may additionally contain an acid such as adipic, citric or tartaric acid or a hydrolysable salt such as zinc chloride or aluminium chloride. Other optional ingredients include solubilizers such as lactic acid diethylamide, astringents such as hamamelis extract or menthol, antiseptics such as boric acid, camphor, 8-hydroxyquinoline sulphate or p-hydroxybenzoic acid, and perfumes.
GB10585/63A 1962-04-12 1963-03-18 2-benzyl-2-imidazoline compounds and compositions including them Expired GB1026778A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM52484A DE1150180B (en) 1962-04-12 1962-04-12 Preparations for pre-treating the skin for shaving

Publications (1)

Publication Number Publication Date
GB1026778A true GB1026778A (en) 1966-04-20

Family

ID=7307429

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10585/63A Expired GB1026778A (en) 1962-04-12 1963-03-18 2-benzyl-2-imidazoline compounds and compositions including them

Country Status (4)

Country Link
US (1) US3354175A (en)
CH (1) CH477448A (en)
DE (1) DE1150180B (en)
GB (1) GB1026778A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5164406A (en) * 1988-06-02 1992-11-17 Bristol-Myers Squibb Co. Method for enhancing transdermal penetration and compositions useful therein
GB2249265B (en) * 1990-10-30 1993-04-28 George Garrett Shaving lotion

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3846554A (en) * 1972-12-15 1974-11-05 Cincinnati Milacron Inc Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation
US3949067A (en) * 1974-06-14 1976-04-06 Gibbs Harold E Shaving lubricant
US4185086A (en) * 1978-05-04 1980-01-22 Johnson & Johnson Talc compositions
US4457912A (en) * 1982-08-24 1984-07-03 Scodari Nicholas F Electric razor preshave composition
US4540705A (en) * 1983-03-14 1985-09-10 Sterling Drug Inc. Antidepressant imidazolines and related compounds
US4634705A (en) * 1984-06-06 1987-01-06 Abbott Laboratories Adrenergic amidines
US6410562B1 (en) 1998-12-18 2002-06-25 Eli Lilly And Company Hypoglycemic imidazoline compounds
US20040009976A1 (en) * 2002-04-30 2004-01-15 Kumiko Takeuchi Hypoglycemic imidazoline compounds
AU2007209382A1 (en) * 2006-01-27 2007-08-02 F. Hoffmann-La Roche Ag Use of 2-imidazoles for the treatment of CNS disorders
KR101176699B1 (en) * 2006-10-19 2012-08-23 에프. 호프만-라 로슈 아게 Aminomethyl-4-imidazoles
KR101172940B1 (en) * 2006-10-19 2012-08-10 에프. 호프만-라 로슈 아게 Aminomethyl-2-imidazoles with affinity with the trace amine associated receptors
ATE533755T1 (en) * 2006-11-02 2011-12-15 Hoffmann La Roche SUBSTITUTED 2-IMIDAZOLES AS MODULATORS OF RECEPTORS ASSOCIATED WITH TRACE AMINES
RU2456281C2 (en) * 2006-11-16 2012-07-20 Ф. Хоффманн-Ля Рош Аг Substituted 4-imidazoles, method for preparing and using them
BRPI0720047A2 (en) * 2006-12-13 2013-12-24 Hoffmann La Roche 2-IMMEDAZOLE AS BINDERS FOR TRACE AMINE RECEIVERS (TAAR)
US20080146523A1 (en) * 2006-12-18 2008-06-19 Guido Galley Imidazole derivatives
CA2675221C (en) * 2007-02-02 2016-02-23 F. Hoffmann-La Roche Ag Novel 2-aminooxazolines as taar1 ligands
KR101222412B1 (en) * 2007-02-15 2013-01-15 에프. 호프만-라 로슈 아게 2-aminooxazolines as taar1 ligands
WO2009003868A2 (en) 2007-07-02 2009-01-08 F. Hoffmann-La Roche Ag 2 -imidazolines having a good affinity to the trace amine associated receptors (taars)
CA2691704A1 (en) * 2007-07-03 2009-01-08 F. Hoffmann-La Roche Ag 4-imidazolines and their use as antidepressants
BRPI0813837A2 (en) * 2007-07-27 2015-01-06 Hoffmann La Roche 2-AZETIDINAMETANOAMINES and 2-PYROLIDINAMETANOAMINES as TAAR LEADERS
WO2009016088A1 (en) * 2007-08-02 2009-02-05 F. Hoffmann-La Roche Ag The use of benzamide derivatives for the treatment of cns disorders
JP5341084B2 (en) * 2007-08-03 2013-11-13 エフ．ホフマン−ラ ロシュ アーゲー Pyridinecarboxamide and benzamide derivatives as TAAR1 ligands
US8242153B2 (en) * 2008-07-24 2012-08-14 Hoffmann-La Roche Inc. 4,5-dihydro-oxazol-2YL derivatives
RU2513086C2 (en) * 2008-07-24 2014-04-20 Ф.Хоффманн-Ля Рош Аг 4,5-dihydro-oxazol-2-yl derivatives
US20100311798A1 (en) * 2009-06-05 2010-12-09 Decoret Guillaume 2-aminooxazolines as taar1 ligands
US8354441B2 (en) * 2009-11-11 2013-01-15 Hoffmann-La Roche Inc. Oxazoline derivatives
US9452980B2 (en) 2009-12-22 2016-09-27 Hoffmann-La Roche Inc. Substituted benzamides
CN102174316A (en) * 2011-03-14 2011-09-07 长江大学 Method for preparing corrosion inhibitor for resisting carbon dioxide/hydrogen sulfide coexistence corrosion
AU2017234042B2 (en) 2016-03-17 2020-11-19 F. Hoffmann-La Roche Ag 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of TAAR

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731471A (en) * 1956-01-17 Nxg hi
CH204725A (en) * 1935-07-23 1939-05-15 Chem Ind Basel Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204728A (en) * 1935-07-23 1939-05-15 Chem Ind Basel Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
US2948724A (en) * 1958-04-21 1960-08-09 Sahyun Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5164406A (en) * 1988-06-02 1992-11-17 Bristol-Myers Squibb Co. Method for enhancing transdermal penetration and compositions useful therein
GB2249265B (en) * 1990-10-30 1993-04-28 George Garrett Shaving lotion

Also Published As

Publication number Publication date
DE1150180B (en) 1963-06-12
US3354175A (en) 1967-11-21
CH477448A (en) 1969-08-31

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