Source: http://www.google.com/patents/US6946005?dq=U.S.+Patent+%23+5,723,324
Timestamp: 2017-04-26 04:26:08
Document Index: 274382490

Matched Legal Cases: ['Application No. 09', 'Application No. 09', 'Application No. 10', 'Application No. 10', 'Application No. 10', 'Application No. 10', 'Application No. 10']

Patent US6946005 - Pyrrolidinyl-substituted para-phenylenediamine derivatives substituted with ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsNovel pyrrolidinyl-substituted para-phenylenediamine derivatives comprising a cationic radical, the dye compositions comprising them and the process for dyeing keratin fibers using these compositions, making it possible to obtain a chromatic, powerful, unselective and fast coloration of keratin fibe...http://www.google.com/patents/US6946005?utm_source=gb-gplus-sharePatent US6946005 - Pyrrolidinyl-substituted para-phenylenediamine derivatives substituted with a cationic radical, and use of these derivatives for dyeing keratin fibersAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS6946005 B2Publication typeGrantApplication numberUS 10/397,245Publication dateSep 20, 2005Filing dateMar 27, 2003Priority dateMar 27, 2002Fee statusLapsedAlso published asUS20030229949, US20040194227Publication number10397245, 397245, US 6946005 B2, US 6946005B2, US-B2-6946005, US6946005 B2, US6946005B2InventorsStéphane Sabelle, Laure Ramos, Madeleine Leduc, Michel PhilippeOriginal AssigneeL'oreal S.A.Export CitationBiBTeX, EndNote, RefManPatent Citations (100), Non-Patent Citations (82), Referenced by (15), Classifications (29), Legal Events (6) External Links: USPTO, USPTO Assignment, EspacenetPyrrolidinyl-substituted para-phenylenediamine derivatives substituted with a cationic radical, and use of these derivatives for dyeing keratin fibers
2 g of 1-fluoro-4-nitrobenzene (0.0155 mol), 1.3 g of sodium hydrogen carbonate (0.0155 mol) and 15 ml of a dioxane/water mixture (8/2) were placed in a three-necked flask. 1.35 g of 3-pyrrolidinol (0.0155 mol) was rapidly added to this mixture. The heterogeneous mixture was heated at reflux (87° C.) for 10 hours. The reaction mixture was then poured into ice-water; a yellow precipitate was obtained, which was filtered off and rinsed with water. After drying under vacuum in the presence of P2O5, 2.95 g of a yellow solid are obtained (97% yield).
40 ml (0.516 mol) of mesyl chloride was added dropwise at 5° C. to 83.3 g (0.4 mol) of N-(4-nitrophenly)-3-hydroxypyrrolidine (1) dissolved in 625 ml of anhydrous THF and 72.7 ml (0.6 mol) of triethylamine. The mixture was allowed to return to room temperature and was then poured onto ice. After filtering off the precipitate by suction and drying, 109 g of yellow powder (2) was obtained.
Melting point: 203° C.
23 g (0.08 mol) of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulphonate (2) was heated for 8 hours at 85° C. in 150 g of 1-methylimidazole (1.82 mol). This solution was stirred in 2 l of ethyl acetate to the point of crystallization. After filtration and drying, 24 g of yellow powder (3) was obtained.
5 g (0.0174 mole) of methanesulfonic acid 1-(4-nitro-phenyl)-pyrrolidin-3yl ester (2) were heated 2 hours at 85° C. in 30 ml of pyrrolidine. The mixture was then poured on ice water until crystallization occurred. After filtrating and drying, the obtained yellow powder was chromatographed with an eluent consisting of dichloromethane/methanol (98/2). 2.6 g of derivative (1) was thus obtained (yield 53%).
melting point=114° C.
35.56 g (0.16 mole) of 1-(3-Methyl-4-nitro-phenyl)-pyrrolidin-3-ol (1) in 500 ml of anhydrous THF and 29 ml (0.24 mole) of triethylamine were mixed drop to drop with 16 ml (0.21 mole) of mesyl chloride at 5° C.
6 g (0.02 mole) of 1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl methane sulfonic ester (2) were heated 12 hours at 90° C. in 30 ml of 1-methylimidazole. The solution was agitated in 2 l of ethylacetate until crystallization. After filtering off and drying, 6.6 g of a yellow powder were obtained (3).
After dissolving 56.4 g of 1-fluoro-4-nitrobenzene (0.4 mol) and 51.2 g of 3-acetamidopyrrolidine (0.4 mol) in 400 ml of NMP, 66.4 g of potassium carbonate (0.48 mol) were added under a nitrogen atmosphere and the mixture was heated at 100° C. for 18 hours. The reaction medium was allowed to cool and was then poured into 2 l of water. The yellow precipitate formed was filtered off, washed with water and then dried in a vacuum oven over P2O5. 100 g (100%) of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (1) was thus obtained in the form of a yellow solid.
100 g (0.4 mol) of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (1) was placed in suspension in a solution containing 300 ml of 37% hydrochloric acid and 660 ml of water in a 2 l three-necked flask. The reaction medium was heated at 90° C. for 7 hours 45 minutes. After cooling, the medium was neutralized gently with 300 ml of aqueous 35% sodium hydroxide (pH=8 approximately). The resulting solid was subsequently filtered off and then washed with water until the washing waters were neutral. The product was then dried under vacuum over P2O5. 74 g (89%) of 1-(4-nitrophenyl)pyrrolidin-4-ylamine (2) was thus obtained in the form of a yellow solid.
2.07 g (0.01 mol) of [1-(4-nitrophenyl)pyrrolidin-3-yl]amine (2) was heated to 90° C. in 10 ml of DMF. 1.32 g (0.0009 mol) of 1-amidinopyrazole monohydrochloride was added slowly to the reaction medium. The mixture was heated for 8 hours. A yellow solid was thus precipitated. The solid thus obtained was filtered off, washed with ethanol and dried under vacuum to give 2 g of a yellow powder (3) (70%).
1.14 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate (0.004 mol), 0.01 g of sodium iodate and 5 g (0.059 mol) of thiazole were placed in a three-necked flask. The heterogeneous mixtures was heated at 110° C. for 18 hours. The reaction mixture was then poured into 100 ml of ethylacetate; a yellow precipitate was then obtained which was filtered off and rinsed with water. After drying under vacuum in the presence of P2O5, 1 g of a yellow solid was obtained. The obtained yellow solid was then recrystallized in isopropanol.
7 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate (0.0244 mol) and 60 ml of pyridin were placed in a three-necked flask. The mixture was heated at 100° C. for 16 hours. The precipitate was filtered off. After washing with ether and drying, 8.5 g of a yellow powder was obtained. The powder was solubilized in 200 ml of water, the solution was then passed through a IRA402 resin. After evaporating and drying, 5.4 g of 1-[1-(4-nitrophenyl)pyrrolidin-3-yl]pyridinium chloride was obtained. (1)
4.3 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate (0.015 mol), 15 ml of methylethylacetone and 0.56 g (0.005 mol) of 1,4 diazabicyclo-2,2,2-octane were placed in a three-necked flask. The heterogeneous mixture was heated at 95° C. for 10 hours. The reaction mixture was then poured into 150 ml of water; the mixture was filtered off, the aqueous phase was extracted with butanol then concentrated; 0.8 g of a yellow powder was thus obtained after drying corresponding to 1-[1-(4-nitrophenyl)pyrrolidin-3-yl]-4-aza-1-azoniabicyclo[2,2,2]octane; methanesulfonate (1).
The following compositions 1 to 20 were prepared. The amounts of each base and coupler are listed in moles (1×10−3 moles) relative to the total composition.
ethanol at 96°
(*) Dyeing medium (2) pH 7 Ethanol 96°
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Hiller et al., "Electron Density Distribution In Hetrocyclic Systems With Two Adjacent Nitrogen Atoms", Chemistry of Heterocyclic Compounds, pp. 93-96, 1965.81Thomas Kauffman et al., "Synthese von Amidrazonen aus Nitrilen und Natriumhydrazid", Chemische Berichte, pp 3436-3443, 1964.82Victor Cohen, "A New Method of Synthesis of Some 2-Aryl and 2-Heterocyclic Benzimidazole, Benzoxazole and Benzothiazole Derivatives", Journal of Heterocyclic Chemistry, 16, pp. 13-16, 1979.Referenced byCiting PatentFiling datePublication dateApplicantTitleUS7132534 *Jul 7, 2003Nov 7, 2006L'orealPara-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibersUS7132543 *Mar 29, 2004Nov 7, 2006L'oreal S.A.Para-phenylenediamine derivatives containing a disubstituted pyrrolidinyl group bearing a cationic radical, and use of the same for dyeing keratin fibersUS8388698Oct 19, 2011Mar 5, 2013L'orealEmulsion dyeing composition containing at least one polyamine, at least one nonionic surfactant and at least one carboxylic acid, and method of using sameUS8394152Jun 24, 2011Mar 12, 2013L'orealEmulsion dyeing composition containing at least one amine, at least one nonionic surfactant and at least one carboxylic acid, and method of using sameUS8506650Jun 24, 2011Aug 13, 2013L'orealEmulsion dyeing composition containing at least one polyamine, at least one nonionic surfactant and at least one phosphate ester, and method of using sameUS8512419Jun 24, 2011Aug 20, 2013L'orealEmulsion dyeing composition containing at least one phospholipid, at least one nonionic surfactant and at least one phosphate ester, and method of using sameUS8518124Jun 24, 2011Aug 27, 2013L'orealEmulsion dyeing composition containing at least one quaternary amine, at least one nonionic surfactant and at least one phosphate ester, and method of using sameUS8518125Oct 19, 2011Aug 27, 2013L'orealEmulsion dyeing composition containing at least one phospholipid, at least one nonionic surfactant and at least one carboxylic acid, and method of using sameUS8523954Jun 24, 2011Sep 3, 2013L'orealEmulsion dyeing composition containing at least one polyamine, at least one nonionic surfactant and at least one silicone, and method of using sameUS8523955Jun 24, 2011Sep 3, 2013L'orealEmulsion dyeing composition containing at least one fatty quaternary amine, at least one nonionic surfactant and at least one silicone, and method of using sameUS8529636Jun 24, 2011Sep 10, 2013L'orealEmulsion dyeing composition containing at least one phospholipid, at least one nonionic surfactant and at least one silicone, and method of using sameUS8540782Oct 19, 2011Sep 24, 2013L'orealEmulsion dyeing composition containing at least one quarternary amine, at least one nonionic surfactant and at least one carboxylic acid and method of using the sameUS20040077852 *Jul 7, 2003Apr 22, 2004Stephane SabellePara-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibersUS20040248961 *Mar 29, 2004Dec 9, 2004Laure RamosPara-phenylenediamine derivatives containing a disubstituted pyrrolidinyl group bearing a cationic radical, and use of the same for dyeing keratin fibersUS20060270691 *Jul 19, 2006Nov 30, 2006Vernalis Research LimitedPurine derivatives as purinergic receptor antagonists* Cited by examinerClassifications U.S. Classification8/405, 8/406, 548/557, 8/410, 8/574, 8/409, 8/540International ClassificationC07F9/572, C07D207/14, C07D401/04, C07D487/08, C07D417/04, C07D521/00Cooperative ClassificationC07D231/12, C07F9/5725, C07D401/04, C07D233/56, C07D207/14, C07D487/08, C07D417/04, C07D249/08European ClassificationC07D207/14, C07F9/572K2, C07D249/08, C07D233/56, C07D231/12, C07D401/04, C07D417/04, C07D487/08Legal EventsDateCodeEventDescriptionJul 22, 2003ASAssignmentOwner name: L OREAL S.A., FRANCEFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SABELLE, STEPHANE;RAMOS, LAURE;LEDUC, MADELEINE;AND OTHERS;REEL/FRAME:014309/0403;SIGNING DATES FROM 20030422 TO 20030424Owner name: L OREAL S.A., FRANCEFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SABELLE, STEPHANE;RAMOS, LAURE;LEDUC, MADELEINE;AND OTHERS;SIGNING DATES FROM 20030422 TO 20030424;REEL/FRAME:014309/0403Jun 6, 2006CCCertificate of correctionFeb 18, 2009FPAYFee paymentYear of fee payment: 4May 3, 2013REMIMaintenance fee reminder mailedSep 20, 2013LAPSLapse for failure to pay maintenance feesNov 12, 2013FPExpired due to failure to pay maintenance feeEffective date: 20130920RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services