US2191978A - Quaternary nitrogen compounds and process of preparing them - Google Patents
Quaternary nitrogen compounds and process of preparing them Download PDFInfo
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- US2191978A US2191978A US104334A US10433436A US2191978A US 2191978 A US2191978 A US 2191978A US 104334 A US104334 A US 104334A US 10433436 A US10433436 A US 10433436A US 2191978 A US2191978 A US 2191978A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/06—Protein or carboxylic compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- the present invention relates to quaternary nitrogen compounds and to a process of preparin: them.
- quaternary nitrogen compounds in which several carboxylic groups or their functional derivatives are united through carbon links with the quaternary nitrogen atom, are manufactured by causing a halogencarboxylic acid, or a salt or ester thereof to act upon a disubstituted amino-acylamide obtainable, for instance, by reaction of halogen-acylamides with secondary amines according to the scheme R1 R4 R
- R1, R2, Ra, R4 and R5 have the abovementioned signification
- R6 represents an aliphatic hydrocarbon radical and X stands for COOK, COO metal atom, esterified COOH.
- the two components may be caused to react in the presence or absence of a suitable solvent or diluent, for example, in water or in an organid solvent, generally at a temperature of 30 C.120 C.
- a suitable solvent or diluent for example, in water or in an organid solvent, generally at a temperature of 30 C.120 C.
- the reaction takes place already when mixing the reaction agents or heating under pressure may be necessary.
- Disubstituted amino-acylamides suitable for the reaction are for example: dimethylaminoacetobutylamide, dimethylamino aceto oleylamide, dimethylamino aceto methyl stearylmide, beta-diethylaminiopropionyldodecylamidle, alpha-dimethylaminostearylamide.
- These disubstituted amino-acylamides may be obtained in a smooth reaction by causing a secondary amine to react with a halogen-amide, for example: chloracetic acid butylamide, alphachloropropionic acid ethanolamide, beta-chloropropionic acid diethanolamide, chloracetic acid paratoluidide, chloracetic acid stearylamide, the amide mixture from chloracetic acid and the primary amines obtainable from palmnut oil fatty acid, chloracetic acid methylstearylamide, alphachloropropionic acid oleylamide, alpha-bromostearic acid amide and others.
- a halogen-amide for example: chloracetic acid butylamide, alphachloropropionic acid ethanolamide, beta-chloropropionic acid diethanolamide, chloracetic acid paratoluidide, chloracetic acid stearylamide, the amide mixture from chloracetic acid and the primary amines obtainable from palmnut oil fatty acid
- reaction with the secondary amines proceeds in some cases without external heat supply, and so rapidly that the heat evolved must be led away, and in other cases the components must be heated together, under pressure if necessary.
- the reaction may also be carried out in the presence of solvents.
- the application of an agent for binding hydrogen halide is useful, if the secondary base is not used in excess.
- Suitable halogen-carboxylic acids are for example: chloracetic acid, beta-chloropropionic acid, alpha-bromo-stearic acid and suitable derivatives are the salts, or esters of these acids.
- the number of the components suitable for the manufacture of the quaternary nitrogen compounds is not limited to the above-named compounds.
- the quaternary nitrogen compounds obtainable by the present invention are in the pure state colorless, in part crystallizable, in part oily to fattyor wax-like bodies which in general are soluble in water or, especially those of high molecular weight, disperse in water so as to form an emulsion.
- the new nitrogen compounds are, for instance, suitable for use in the textile industry.
- the dimethylamino-acetostearylamide is obtained by treating in a pressure vessel for 3 hours at a temperature of 80-100 C. 328 parts of chloracetostearylamide with 220 parts of a solution of dimethylamine of 45 per cent strength. After distillation of the solvent, the dimethylamine hydrochloride formed as a by-product is extracted by means of hot water (with addition of sodium chloride) at C. The separated oil solidifies after cooling and is pure dimethylamino-acetostearylamide. The yield almost corresponds with that foretold by theory.
- the dimethylamino-acetobutylamide is obtained by introducing 150 parts of chloraceto butylamide, while cooling, into a solution of 50 parts of dimethylamine in 500 parts of alcohol. With gradual evolution of heat which is first restrained by cooling, a complete conversion to dimethylaminoacetobutylamide occurs. The product is worked up by removing the solvent and stirring the remaining mass with hot water in order to extract the dimethylamine hydrochloride. The yield of dimethylamino-acetobutylamide which remains is very good.
- N-dimethyl-N- acetostearylamide-betaine dodecyl ester chloride is a wax-like body, which forms a dispersion in water which resembles an emulsion.
- the solution may be adjusted to any desired concentration or dried to form a powder.
- the diethylamino-acetododecylamide is ob tainable by treating 260 parts of chloracetododecylamide (obtainable by causing dodecylamine to react with chloracetyl chloride in the presence of dimethylaniline) with parts of diethylamine in a pressure vessel for three hours at 100 C.
- the diethylamine hydrochloride formed is eliminated by stirring the mass with hot water and the diethylamino-acetododecylamide is separated which ina hot state'is an oily substance.
- the product is dried and is then sufficiently pure for being worked up. It may be distilled under reduced pressure and boils under a pressure of 2 mm., of mercury at a temperature of 174 C. The yield is nearly quantitative.
- the dimethylamine-acetododecylamide is obtained by mixing 130 parts of chloracetododecylamide with 110 parts of a solution of 46 per cent. strength of dimethylamine in methanol. After a short time the reaction occurs with evolution 01' heat which is best allowed to end in a closed vessel at 70 C., whereupon the whole is heated for 1 hour at the same temperature. After the solvent has been removed, the dimethylaminohydrochloride is separated from the mass by stirring with hot water, the dimethylamino-acetododecylamide remaining in a pure form. It is oily when hot and, on cooling, solidifies to colorless clustered crystals. It may be distilled under a pressure of 2 mm. of mercury at a temperature of -172 C.
- beta-chloropropionic acid diethanolamide (obtainable by causing diethanolamine to react with beta-chloropropionyl chloride) are treated together with 230 parts of a solution of 45 per cent. by weight of dimethylamine in methanol for three hours in a closed vessel at about 80 C. After cooling, the solvent is removed by distillation, the remaining mass is poured into water and the whole is mixed with 115 parts of caustic soda solution of 36 per cent. strength in order to convert the hydrochloride of the dimethylamine into the free base. The dimethylamine is removed by distillation, the water and the sodium chloride are then eliminated, and the dimethylamino-propionyl-diethanolamide remains as an oily substance.
- 362 parts of alpha-bromostearic acid amide are treated with 250 parts of a solution of 45 per cent. by weight of dimethylamine in methanol for 5 hours in' a pressure vessel at IOU-130 C. After distillation of the solvent and of the amine in excess, the hydrobromide of the dimethylamine, which is formed as by-product, is eliminated by extraction with hot water. After drying, the alpha-dimethylaminostearylamide remains with a good yield.
- R alkyl R5 wherein R1 and R2 represent alkyl radicals, R4 a member of the group consisting of hydrogen, hydrocarbon radicals and aliphatic hydrocarbon radicals substituted by hydroxy groups and R5 represents an alkyl radical of at least 8 carbon atoms
- X being a member of the group consisting of COOH, COO metal atom, esterified COOH, the products being in the pure state colorless compounds.
- R5 representing an alkyl radical of at least 8 carbon atoms and X being a member of the group consisting of COOH, COO metal atom, esterified COOH the products being in the pure state colorless compounds.
Description
Patented Feb. 27, 1940 QUATEBNABY NITROGEN COMPOUNDS AND PROCESS OF PREPARING THEM Gerhard Belle, Frankfort-on-the-Maln, and Karl Horst, Hofheim in Taunus, Germany, assignors to I. G. Farbenlndustrle Aktiengesellschaft, Frankfort-on-thc-Main, Germany No Drawing. Application October c, 1936, Se-
rial No. 104,884. In Germany October 10,
1985 5 Claims.
The present invention relates to quaternary nitrogen compounds and to a process of preparin: them.
We have found that quaternary nitrogen compounds in which several carboxylic groups or their functional derivatives are united through carbon links with the quaternary nitrogen atom, are manufactured by causing a halogencarboxylic acid, or a salt or ester thereof to act upon a disubstituted amino-acylamide obtainable, for instance, by reaction of halogen-acylamides with secondary amines according to the scheme R1 R4 R| R6 NH+halogen RaCO.N /N.R;.C ONiH halogen Y wherein R3 stands for an aliphatic hydrocarbon radical. R1 and R: stand for hydrocarbon radicals which may be substituted and R4 and R5 it stand for hydrogen or a hydrocarbon radical which may be substituted.
The formation of the quaternary nitrogen compounds according to the present invention corresponds to the following scheme:
wherein R1, R2, Ra, R4 and R5 have the abovementioned signification, R6 represents an aliphatic hydrocarbon radical and X stands for COOK, COO metal atom, esterified COOH.
The two components may be caused to react in the presence or absence of a suitable solvent or diluent, for example, in water or in an organid solvent, generally at a temperature of 30 C.120 C. Depending on the nature of the parent materials, the reaction takes place already when mixing the reaction agents or heating under pressure may be necessary.
Disubstituted amino-acylamides suitable for the reaction are for example: dimethylaminoacetobutylamide, dimethylamino aceto oleylamide, dimethylamino aceto methyl stearylmide, beta-diethylaminiopropionyldodecylamidle, alpha-dimethylaminostearylamide.
These disubstituted amino-acylamides may be obtained in a smooth reaction by causing a secondary amine to react with a halogen-amide, for example: chloracetic acid butylamide, alphachloropropionic acid ethanolamide, beta-chloropropionic acid diethanolamide, chloracetic acid paratoluidide, chloracetic acid stearylamide, the amide mixture from chloracetic acid and the primary amines obtainable from palmnut oil fatty acid, chloracetic acid methylstearylamide, alphachloropropionic acid oleylamide, alpha-bromostearic acid amide and others. The reaction with the secondary amines proceeds in some cases without external heat supply, and so rapidly that the heat evolved must be led away, and in other cases the components must be heated together, under pressure if necessary. The reaction may also be carried out in the presence of solvents. The application of an agent for binding hydrogen halide is useful, if the secondary base is not used in excess.
Suitable halogen-carboxylic acids are for example: chloracetic acid, beta-chloropropionic acid, alpha-bromo-stearic acid and suitable derivatives are the salts, or esters of these acids.
The number of the components suitable for the manufacture of the quaternary nitrogen compounds is not limited to the above-named compounds. There may also be used amino-acylamides disubstituted in the amino-groups by aryl or aralkyl; the amide radical may also contain any other substituents. Furthermore, there may be used any halogen-carboxylic acid which contains a reactive halogen atom.
The quaternary nitrogen compounds obtainable by the present invention are in the pure state colorless, in part crystallizable, in part oily to fattyor wax-like bodies which in general are soluble in water or, especially those of high molecular weight, disperse in water so as to form an emulsion.
The new nitrogen compounds are, for instance, suitable for use in the textile industry.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:
(1) 337 parts of dimethylamino-acetostearylamide are gradually mixed, in the form of a melt at '75-85 0., with 110 parts of chloracetic acid methyl ester and the mixture is then heated for two hours at 95-100 C. and finally for two hours at 110-120 C.; during this time the mass which becomes more and more viscous must be mixed by stirring or kneading. The N-dimethyl-N- acetostearylamide-betaine methyl ester chloride thus obtained solidifies on cooling and may be pulverized. It yields clear solutions with water. The yield is quantitative.
The dimethylamino-acetostearylamide is obtained by treating in a pressure vessel for 3 hours at a temperature of 80-100 C. 328 parts of chloracetostearylamide with 220 parts of a solution of dimethylamine of 45 per cent strength. After distillation of the solvent, the dimethylamine hydrochloride formed as a by-product is extracted by means of hot water (with addition of sodium chloride) at C. The separated oil solidifies after cooling and is pure dimethylamino-acetostearylamide. The yield almost corresponds with that foretold by theory.
(2) 158 parts of dimethylamino-acetobutylamide are gradually mixed, while vigorously stirring, in a vessel provided with a reflux condenser with 122 parts of chloracetic acid ethyl ester, the condensation occurring with evolution of heat.
Care must be taken by suitably cooling that the temperature remains within moderate limits and does not exceed 120 C. Stirring is then continued for l-2 hours at -l20 C., the yield of the N-dimethyl-N-acetobutylamide-betaine ethyl ester chloride, which is soluble in water to a clear solution, is very good.
The dimethylamino-acetobutylamide is obtained by introducing 150 parts of chloraceto butylamide, while cooling, into a solution of 50 parts of dimethylamine in 500 parts of alcohol. With gradual evolution of heat which is first restrained by cooling, a complete conversion to dimethylaminoacetobutylamide occurs. The product is worked up by removing the solvent and stirring the remaining mass with hot water in order to extract the dimethylamine hydrochloride. The yield of dimethylamino-acetobutylamide which remains is very good.
(3) 363 parts of dimethylamino-aceto-o1eylamide obtainable by causing chloraceto-oleylamide to react with dimethylamine are gradually mixed at 40-50 C. with a solution of 106 parts of sodium chloracetate in 1000 parts of water and the mixture is heated for 4-6 hours at 80- 90 C., the dimethylaminoaceto-oleylamlde dissolving to a clear solution; the condensation leads to the sodium salt of N-dimethyl-N-acetooleylmethylstearylamide to react with dimethylamine, are dissolved in 700 parts of warm toluene and the solution is gradually mixed, while stirring, in a reflux apparatus with 110 parts of chloracetic acid methylester, the temperature being first kept at 75-90" C. and finally, for two hours, at 110 C. After the solvent has been removed, the N-dimethyl-N-acetomethylstearylamide betaine methyl ester chloride is obtained with a good yield.
(6) 674 parts of dimethylaminoacetostearylamide are gradually mixed, while vigorously stirring, at 70 C. with 522 parts of chloracetic acid doclecyl ester, and the whole is after-heated for 3 hours at IOU-110 C. The N-dimethyl-N- acetostearylamide-betaine dodecyl ester chloride is a wax-like body, which forms a dispersion in water which resembles an emulsion.
('7 350 parts of beta-dimethylaminopropionylstearylamide, obtainable by causing beta-chloropropionic acid stearylamide to react with dimethylamine, are heated with 108 parts of chloracetic acid methyl ester as described in Example 1. The N-dimethyl-N-propionylstearylamide-betaine methyl ester chloride is analogously obtained with a very good yield in the form of a fat-like compound, which dissolves in water to a clear solution.
8) 380 parts of a tertiary polyamine, obtainable by heating for several hours at 70-100 C. 350 parts of chloracetostearylamide and parts of a polyethylene-polyamine, consisting substantially of diethylenetriamine, are heated with 75 parts of chloracetic acid methyl ester for 2 hours at YO-100 C. A wax-like product of high molecular weight is obtained with a good yield which dissolves in water to a clear solution and has a good frothing power; the product obtained corresponds to the formula:
amide-betaine chloride. The solution may be adjusted to any desired concentration or dried to form a powder.
(4) 297 parts of diethylamino-acetododecylamide are mixed, while stirring, at 70-90 C. with 153 parts of bromacetic methyl ester in small portions. The condensation is completed by after-heating at 120 C. for two hours. The N-diethyl-N-acetododecylamide betaine methyl ester bromide is obtained with a good yield.
The diethylamino-acetododecylamide is ob tainable by treating 260 parts of chloracetododecylamide (obtainable by causing dodecylamine to react with chloracetyl chloride in the presence of dimethylaniline) with parts of diethylamine in a pressure vessel for three hours at 100 C. The diethylamine hydrochloride formed is eliminated by stirring the mass with hot water and the diethylamino-acetododecylamide is separated which ina hot state'is an oily substance. The product is dried and is then sufficiently pure for being worked up. It may be distilled under reduced pressure and boils under a pressure of 2 mm., of mercury at a temperature of 174 C. The yield is nearly quantitative.
5) 351 parts of dimethylamino-acetomethylstearylamide, obtainable by causing chloraceto- CH: (IJH C1 ([3111 $0 (")0 ('30 O CH; O CH; 0 CH3 (9) 269 parts of dimethylamino-acetododecylamide are dissolved in 800 parts of alcohol; 386 parts of sodium alphabromostearate are gradually added and the whole is heated, while stirring, for 6 hours in a reflux apparatus. After the alcohol has been removed by distillation, the sodium salt of N-dimethyl-N-acetododecylamide-stearylbetaine bromide is obtained with a good yield; on account of its high molecular weight it is soluble in water in a hot state only.
The dimethylamine-acetododecylamide is obtained by mixing 130 parts of chloracetododecylamide with 110 parts of a solution of 46 per cent. strength of dimethylamine in methanol. After a short time the reaction occurs with evolution 01' heat which is best allowed to end in a closed vessel at 70 C., whereupon the whole is heated for 1 hour at the same temperature. After the solvent has been removed, the dimethylaminohydrochloride is separated from the mass by stirring with hot water, the dimethylamino-acetododecylamide remaining in a pure form. It is oily when hot and, on cooling, solidifies to colorless clustered crystals. It may be distilled under a pressure of 2 mm. of mercury at a temperature of -172 C.
Analogously to the manufacture of the dimethyl-amino-acetododecylamide the following disubstituted amino-acylamides may be prepared:
200 parts of beta-chloropropionic acid diethanolamide (obtainable by causing diethanolamine to react with beta-chloropropionyl chloride) are treated together with 230 parts of a solution of 45 per cent. by weight of dimethylamine in methanol for three hours in a closed vessel at about 80 C. After cooling, the solvent is removed by distillation, the remaining mass is poured into water and the whole is mixed with 115 parts of caustic soda solution of 36 per cent. strength in order to convert the hydrochloride of the dimethylamine into the free base. The dimethylamine is removed by distillation, the water and the sodium chloride are then eliminated, and the dimethylamino-propionyl-diethanolamide remains as an oily substance.
362 parts of alpha-bromostearic acid amide are treated with 250 parts of a solution of 45 per cent. by weight of dimethylamine in methanol for 5 hours in' a pressure vessel at IOU-130 C. After distillation of the solvent and of the amine in excess, the hydrobromide of the dimethylamine, which is formed as by-product, is eliminated by extraction with hot water. After drying, the alpha-dimethylaminostearylamide remains with a good yield.
We claim: 1. The products of the general formula:
R1 halogen R4 N-R3.CO.N
R2 Ilia 2. The products of the general formula:
R: alkyl R5 wherein R1 and R2 represent alkyl radicals, R4 a member of the group consisting of hydrogen, hydrocarbon radicals and aliphatic hydrocarbon radicals substituted by hydroxy groups and R5 represents an alkyl radical of at least 8 carbon atoms X being a member of the group consisting of COOH, COO metal atom, esterified COOH, the products being in the pure state colorless compounds.
3. The products of the formula:
alkyl C1 H NcH,.co.N (13H: x
R5 representing an alkyl radical of at least 8 carbon atoms and X being a member of the group consisting of COOH, COO metal atom, esterified COOH the products being in the pure state colorless compounds.
4. The product of the formula alkyl R H3O CH: CiaHa'! the product being in the pure state a colorless fat-like body.
5. The product of the formula NCH2.CO.N
CH: Cn u COONa the product being in the pure state a colorless fat-like body.
. GERHARD BAILE.
KARL HORST.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2191978X | 1935-10-10 |
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| Publication Number | Publication Date |
|---|---|
| US2191978A true US2191978A (en) | 1940-02-27 |
Family
ID=7989405
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US104334A Expired - Lifetime US2191978A (en) | 1935-10-10 | 1936-10-06 | Quaternary nitrogen compounds and process of preparing them |
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| Country | Link |
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| US (1) | US2191978A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417513A (en) * | 1939-10-30 | 1947-03-18 | Nelles Johannes | Textile softening with nitrogen containing linear ester polymer |
| US2580411A (en) * | 1948-10-23 | 1952-01-01 | Searle & Co | Dihexyl alanine dialkylamides |
| US2604449A (en) * | 1949-03-08 | 1952-07-22 | Swan Finch Oil Corp | Greases and compounds for making same and other compositions |
| US2647121A (en) * | 1951-02-02 | 1953-07-28 | Ruth P Jacoby | Diamine-bis-acetamides |
| DE2355026A1 (en) * | 1973-11-03 | 1975-05-15 | Henkel & Cie Gmbh | NEW OMEGA-AMINO-CARBONIC ACID AMIDES, THEIR PRODUCTION AND USE AS ANTIMICROBIAL AGENTS |
| US20050239821A1 (en) * | 2002-07-03 | 2005-10-27 | Johan Neyts | Viral inhibitors |
| US20060058202A1 (en) * | 2004-09-13 | 2006-03-16 | Levine Jeffrey A | Alkylaminoacetamide lubricant additives |
| US20070244148A1 (en) * | 2003-12-22 | 2007-10-18 | Bondy Steven S | Imidazo 4,5-C Pyridine Compounds and Methods of Antiviral Treatment |
| US20080188516A1 (en) * | 2004-12-21 | 2008-08-07 | Bondy Steven S | Imiadazo[4,5-c] pyridine compound and method of antiviral treatment |
| US20080199427A1 (en) * | 2006-07-07 | 2008-08-21 | Bondy Steven S | Novel pyridazine compound and use thereof |
| US8106054B2 (en) | 2007-07-06 | 2012-01-31 | Gilead Sciences, Inc. | Crystalline pyridazine compound |
-
1936
- 1936-10-06 US US104334A patent/US2191978A/en not_active Expired - Lifetime
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417513A (en) * | 1939-10-30 | 1947-03-18 | Nelles Johannes | Textile softening with nitrogen containing linear ester polymer |
| US2580411A (en) * | 1948-10-23 | 1952-01-01 | Searle & Co | Dihexyl alanine dialkylamides |
| US2604449A (en) * | 1949-03-08 | 1952-07-22 | Swan Finch Oil Corp | Greases and compounds for making same and other compositions |
| US2647121A (en) * | 1951-02-02 | 1953-07-28 | Ruth P Jacoby | Diamine-bis-acetamides |
| DE2355026A1 (en) * | 1973-11-03 | 1975-05-15 | Henkel & Cie Gmbh | NEW OMEGA-AMINO-CARBONIC ACID AMIDES, THEIR PRODUCTION AND USE AS ANTIMICROBIAL AGENTS |
| US20050239821A1 (en) * | 2002-07-03 | 2005-10-27 | Johan Neyts | Viral inhibitors |
| US8779141B2 (en) | 2002-07-03 | 2014-07-15 | Gilead Sciences, Inc. | Viral inhibitors |
| US7737162B2 (en) | 2002-07-03 | 2010-06-15 | Gilead Sciences, Inc. | Viral inhibitors |
| US7648998B2 (en) | 2003-12-22 | 2010-01-19 | K.U. Leuven Research & Development | Imidazo 4,5-c pyridine compounds and methods of antiviral treatment |
| US20070244148A1 (en) * | 2003-12-22 | 2007-10-18 | Bondy Steven S | Imidazo 4,5-C Pyridine Compounds and Methods of Antiviral Treatment |
| US8329727B2 (en) | 2003-12-22 | 2012-12-11 | Gilead Sciences, Inc. | Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment |
| US20100028301A1 (en) * | 2003-12-22 | 2010-02-04 | Bondy Steven S | IMIDAZO[4,5-c]PYRIDINE COMPOUNDS AND METHODS OF ANTIVIRAL TREATMENT |
| US20060058202A1 (en) * | 2004-09-13 | 2006-03-16 | Levine Jeffrey A | Alkylaminoacetamide lubricant additives |
| US7521403B2 (en) | 2004-09-13 | 2009-04-21 | Ciba Specialty Chemicals Corporation | Alkylaminoacetamide lubricant additives |
| WO2006029966A1 (en) * | 2004-09-13 | 2006-03-23 | Ciba Specialty Chemicals Holding Inc. | Alkylaminoacetamide lubricant additives |
| US7795276B2 (en) | 2004-12-21 | 2010-09-14 | Gilead Sciences, Inc. | Imiadazo[4,5-c] pyridine compound and method of antiviral treatment |
| US20080188516A1 (en) * | 2004-12-21 | 2008-08-07 | Bondy Steven S | Imiadazo[4,5-c] pyridine compound and method of antiviral treatment |
| US20100063059A1 (en) * | 2006-07-07 | 2010-03-11 | Gerhard Puerstinger | Novel pyridazine compound and use thereof |
| US20080199427A1 (en) * | 2006-07-07 | 2008-08-21 | Bondy Steven S | Novel pyridazine compound and use thereof |
| US20100152444A1 (en) * | 2006-07-07 | 2010-06-17 | Gilead Sciences, Inc. | Novel pyridazine compound and use thereof |
| US7754720B2 (en) | 2006-07-07 | 2010-07-13 | Gilead Sciences, Inc. | Pyridazine compound and use thereof |
| US7956184B2 (en) | 2006-07-07 | 2011-06-07 | Gilead Sciences, Inc. | Pyridazine compound and use thereof |
| US8569487B2 (en) | 2006-07-07 | 2013-10-29 | Gilead Sciences, Inc. | Pyridazine compound and use thereof |
| US8106054B2 (en) | 2007-07-06 | 2012-01-31 | Gilead Sciences, Inc. | Crystalline pyridazine compound |
| US8569488B2 (en) | 2007-07-06 | 2013-10-29 | Gilead Sciences, Inc. | Crystalline pyridazine compound |
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