US2670376A - N-alpha-naphthyl n, n' n,'-trialkylethylene diamines - Google Patents
N-alpha-naphthyl n, n' n,'-trialkylethylene diamines Download PDFInfo
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- US2670376A US2670376A US251634A US25163451A US2670376A US 2670376 A US2670376 A US 2670376A US 251634 A US251634 A US 251634A US 25163451 A US25163451 A US 25163451A US 2670376 A US2670376 A US 2670376A
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- United States
- Prior art keywords
- naphthyl
- alpha
- diamines
- trialkylethylene
- compounds
- 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 - Lifetime
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- 150000004985 diamines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 ALPHANAPHTHYL Chemical class 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 230000001408 fungistatic effect Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 244000053095 fungal pathogen Species 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100194817 Caenorhabditis elegans rig-6 gene Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000698776 Duma Species 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PLMOUHDDLVLZMW-UHFFFAOYSA-N n,n'-dimethyl-n'-nonylethane-1,2-diamine Chemical compound CCCCCCCCCN(C)CCNC PLMOUHDDLVLZMW-UHFFFAOYSA-N 0.000 description 1
- XBGVVNLSPSPUSG-UHFFFAOYSA-N n-decyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCCCCCCCCCNCCN(C)C XBGVVNLSPSPUSG-UHFFFAOYSA-N 0.000 description 1
- BOTBDBFBXDILAR-UHFFFAOYSA-N n-hexyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCCCCCNCCN(C)C BOTBDBFBXDILAR-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
Definitions
- R is a longkchain alkyl radical containi'rig 6'to li'ca'rbon atoms
- R "anci"R are short chainalkyl radicals containingl to 3 carbon" atoms.
- R and R1 maybe, but are not necessaril'yal-ike;
- the compounds of our invention have a very.
- Minimal fungistatic concentrations (ma/73) compound is separated and purifiedg' as described in'the specific example below.
- firstthe alkylnaphthylamines by react- 127.5 grams (0.5 mole) of a-naphthyl-octylamine, the above prepared intermediate, was dissolved in 250 mls. of xylene and 23.5 grams (0.6 mole) of sodium amide was added. It was slowly heated up to 90 C. and was kept at that temperature for thirty-six hours. The mixture was allowed to cool to room temperature and 58.75 grams (0.5 mole) of fl-dimethylaminoethyl chloride was added. The reaction mixture was then heated to 105110 C. and kept at that temperature for forty-eight hours under continous stirring.
- the reaction mixture was then allowed to cool to room temperature and acidified to a pH of 1.0 with a 1:1 HCl solution.
- the aqueous layer was separated from the xylene layer, cooled and the pH adjusted to 10.6 with sodium hydroxide solution (40%).
- the aqueous alkaline mixture was extracted three times with ether.
- the combined ether extractions were dried with KOH pellets. After separating from the KOH pellets, the ether was distilled off on the steam bath. The residue was fractionated in vacuum and the fraction between 102-169 C. at 3 mm. was collected.
- the product, N-a-naphthyLN-octyLN,N- dimethylethylenediamine forms a viscous, oily liquid. It was obtained in about 52.3% yield. In a nitrogen determination (Micro-Dumas) there .was found: N:8.39% (theory:8.60%).
- the compounds of our invention present highly valuable and unexpected fungistatic properties especially against pathogenic fungi, although their usefulness is not limited to that particular group.
- R. is an alkyl radical containing 6 to 14 carbon atoms
- R and R are alkyl radicals containing one to three carbon atoms, and their water soluble hydrochlorides.
- the method which comprises reacting a.- naphthylamine with a long chain alkylbromide to produce an alkylnaphthylamine containing a long chain alkyl radical, preparing the sodium salt of the last named compound, and reacting the said sodium salt with p dialkylaminoethylene chloride.
- the method which comprises reacting a.- naphthylamin with a long chain alkylbromide having 6 to 14 carbon atoms to produce an alkylnaphthylamine containing a long chain alkyl radical, preparing the sodium salt of the last named compound, and reacting the said sodium salt with B dialkylaminoethylene chloride in which the alkyl radical contains 1 to 3 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented Feb. 23, 1954 UN IIED oFF'rcE;
N-ALPHA-NAPHTHYL N,-l l.N', -TRIALKYL- ETHYLENE DIAMINES- John'V. S cudi and Godfrey E'Grail; Bronx, N. Y'., assignors "to Nepera Chemical: 06. Ina, Nepera Park; Yonkers, N Y., a corporation-of N err-York No Drawing. Applicationoctober 16; 1951, Serial-N0. 251.634
in w-hich R is a longkchain alkyl radical containi'rig 6'to li'ca'rbon atoms, R "anci"R are short chainalkyl radicals containingl to 3 carbon" atoms. R and R1 maybe, but are not necessaril'yal-ike;
The compounds of our invention have a very.
2 ing-a-naphthylamine with along chain alkylbromide in which the alkyl' radical contains 6 t 142 carbon atoms and purify the product by distilla'e tion. Then we prepare the sodium salt of the:- intermediate alkylnaphthylamine by reacting 1 it with sodiumamide. The sodi'umsalt is then reacted with' fi-dialkylaminoethyl chloride inwhich the alkyl radical contains 1 t0"'3 cai bonato'ins' i'n" anonpolar solvent, after which the desir'ed-new remarkable antifungal activity. In vit'ro, they. 7
show fungistatic activityagainst many fungi'even in-a di1ution of 1:400,000; activity-is apparently a function of the .alkylsubstituents in R. In compoundswhere-R is a short chain alkyl radical -likemethyl, ethyl even butyl, the antifungal activity is only slight. Where this radical is hexyl' or ahigher-alkyl group -the -activity surprisingly increases, as can be -seen irom the following table:
Minimal fungistatic concentrations (ma/73) compound is separated and purifiedg' as described in'the specific example below.
The products so obtainedar'e -high boiling,- vis cou's'; oily liquids, soluble in the usual org ni'c solvents. They are insolublein' water; butrorm' a" water soluble addition salt with hydrochloric and other acids.
The following is an illustrative'e'xam'ple 'of our preferred. procedure of carrying out our inverttion, which is given for illustration and notfor' limitation.
Preparation of one of the-intermediates:
300*grams (2.11 moles) of"a'-naphthylamiiie were dissolved in 500'm1s. of ethanol *and' to this 340 grams (1.76 moles) ofoctyl bromide were added; The solution was refluxed for 48 hours after which the ethanol was removed by distillation. The semisolid residue was placed'in 100 mls'wof water which was made alkaline with sodium hydroxide solution l (40%) to pl-I-- 10.0 and In the compounds of this tablelfR and B im both methyl and Ris Fungus Tested .q a.
' iii'th'yl ethyl" lifityl' hexyl 'octyl nonyi decyl Tkichophytcn-menta 4 4 64' o.25 0xfis= 0i'25 0.25'" Trichophytonrubrum; Y 4 s- 4- 0. 25 o;2 5 0szs 0. 5. Spor0t1ichumSchenckn 2 8 16 0,25 ((3.25 Q.25 2 Epidermaphyton flocclisu 2 4 0.5 ().-25 0.25 0. 25 l Microsparum cams"..- 8 8 8 l). 5 1.0 0. 5 4 Microsfibiiti'nadouini-.- 4 8 4 0.25 (L5, 0. 25 2 Candida aZbicans- 1 64 32- 64 2.0 2.0 1.0 8
These in vitro tests against pathogenic fungi thenwaseiitractedthreetimes' with chloroform? indicate the utility of our compounds against The chloroform extracts were combined and fungus infections of the skin. Such infections dried with anhydrous sodium sulfate, filtered and are ringworm of the scalp, barbers itch, athletes the chloroform distilled oif at 60-65 C. The foot and others. We have employed the hydroresidue was distilled in vacuum and the fraction chlorides of our compounds in hydrophilic ointdistilling at ZOO-209 C. at 4 mm. (a-naphthylment with gratifying results. The ointment was octylamine) was collected. The yield obtained made up from 0.5 to 2% in strength. Lotions may be prepared by dissolving our compounds in suitable vehicles.
To prepare the compounds of our invention we was 72.6%. In a nitrogen determination (Micro- Dumas) there was found N=5.10% (theory: 5.47%).
Preparation of one of the products:
prepare firstthe alkylnaphthylamines, by react- 127.5 grams (0.5 mole) of a-naphthyl-octylamine, the above prepared intermediate, was dissolved in 250 mls. of xylene and 23.5 grams (0.6 mole) of sodium amide was added. It was slowly heated up to 90 C. and was kept at that temperature for thirty-six hours. The mixture was allowed to cool to room temperature and 58.75 grams (0.5 mole) of fl-dimethylaminoethyl chloride was added. The reaction mixture was then heated to 105110 C. and kept at that temperature for forty-eight hours under continous stirring. The reaction mixture was then allowed to cool to room temperature and acidified to a pH of 1.0 with a 1:1 HCl solution. The aqueous layer was separated from the xylene layer, cooled and the pH adjusted to 10.6 with sodium hydroxide solution (40%). The aqueous alkaline mixture was extracted three times with ether. The combined ether extractions were dried with KOH pellets. After separating from the KOH pellets, the ether was distilled off on the steam bath. The residue was fractionated in vacuum and the fraction between 102-169 C. at 3 mm. was collected. The product, N-a-naphthyLN-octyLN,N- dimethylethylenediamine forms a viscous, oily liquid. It was obtained in about 52.3% yield. In a nitrogen determination (Micro-Dumas) there .was found: N:8.39% (theory:8.60%).
Preparation of the water soluble hydrochloride of above compound:
3.26 grams (0.01 mole) of N-a-naphthyLN-noctyl,-N',N-dimethylethylenediarnine was dissolved in 50 mls. of dry ether. To this solution was added 0.36 grams (0.01 mole) of HCl dissolved in ether. The solutions were intimately mixed and cooled over night. The precipitate was then collected, washed with dry ether and recrystallized from a mixture of isopropanol and ether. The melting point of the hydrochloride is 102-104 C. In a nitrogen determination (Micro-Dumas) there was found N:'7.60% (theory:7.55%
Following the above procedure, a number of our compounds were prepared, differing in the length of the alkyl radical in the R substitution. They have the following characteristics:
The hydrochloride of the last compound (R=C1oHz1) melts at 93-4 C. In the nitrogen determination was found N:'7.39% (theory:
As can be seen from our specifications the compounds of our invention present highly valuable and unexpected fungistatic properties especially against pathogenic fungi, although their usefulness is not limited to that particular group.
We do not limit ourselves to the specific limitations mentioned, as these are given solely for the purpose of clearly describing our invention as set forth herein.
What we claim is:
1. Compounds of the group consisting of alphanaphthyl, tri-alkylethylenediamines of the general formula:
where R. is an alkyl radical containing 6 to 14 carbon atoms, R and R are alkyl radicals containing one to three carbon atoms, and their water soluble hydrochlorides.
2. N alpha naphthyl N hexyl N',N'- dimethyl-ethylenediamine.
3. N alpha naphthyl N heptyl N',N',- dimethylethylenediamine.
4. N alpha naphthyl N octyl N,N'- dimethylethylenediamine.
5. N alpha naphthyl N nonyl dimethylethylenediamine.
6. N alpha naphthyl N decyl N',N'- dimethylethylenediamine.
'7. The method which comprises reacting a.- naphthylamine with a long chain alkylbromide to produce an alkylnaphthylamine containing a long chain alkyl radical, preparing the sodium salt of the last named compound, and reacting the said sodium salt with p dialkylaminoethylene chloride.
8. The method which comprises reacting a.- naphthylamin with a long chain alkylbromide having 6 to 14 carbon atoms to produce an alkylnaphthylamine containing a long chain alkyl radical, preparing the sodium salt of the last named compound, and reacting the said sodium salt with B dialkylaminoethylene chloride in which the alkyl radical contains 1 to 3 carbon atoms.
JOHN V. SCUDI. GODFREY F. GRAIL.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 1,757,394 Schulemann et al. May 6, 1930 2,121,619 Williams et a1 June 21, 1938 2,430,722 Ladd Nov. 11, 1947 2,451,149 Boehm Oct. 12, 1948 2,457,048 Kyrides et al. Dec. 21, 1948 2,494,355 Paul et al. Jan. 10, 1950 2,536,750 Kamlet Jan. 2, 1951 2,627,491 Szabo et al Feb. 3, 1953 FOREIGN PATENTS Number Country Date 67,972 Denmark Nov. 22, 1948
Claims (1)
1. COMPOUNDS OF THE GROUP CONSISTING OF ALPHANAPHTHYL, TRI-ALKYLETHYLENEDIAMINES OF THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US251634A US2670376A (en) | 1951-10-16 | 1951-10-16 | N-alpha-naphthyl n, n' n,'-trialkylethylene diamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US251634A US2670376A (en) | 1951-10-16 | 1951-10-16 | N-alpha-naphthyl n, n' n,'-trialkylethylene diamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2670376A true US2670376A (en) | 1954-02-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US251634A Expired - Lifetime US2670376A (en) | 1951-10-16 | 1951-10-16 | N-alpha-naphthyl n, n' n,'-trialkylethylene diamines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2670376A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3153093A (en) * | 1961-11-22 | 1964-10-13 | Abbott Lab | Amino derivatives of nu-cyclopropylbenzylamines |
| US3923813A (en) * | 1969-12-19 | 1975-12-02 | Christiaens Sa A | Derivatives of 2-aminoindanes |
| US4209302A (en) * | 1979-05-10 | 1980-06-24 | Morton-Norwich Products, Inc. | Marker for petroleum fuels |
| US20060142387A1 (en) * | 2003-06-10 | 2006-06-29 | Rodolfo Cadilla | Chemical compounds |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1757394A (en) * | 1926-07-08 | 1930-05-06 | Winthrop Chem Co Inc | Aminoalkylamino derivative of aromatic aminohydroxy or polyamino compounds |
| US2121619A (en) * | 1937-09-18 | 1938-06-21 | Du Pont | Preservation of rubber |
| US2151149A (en) * | 1935-05-31 | 1939-03-21 | Rca Corp | Television apparatus |
| US2430722A (en) * | 1946-04-25 | 1947-11-11 | Us Rubber Co | Derivatives of chlorinated quinones as fungicides |
| US2457048A (en) * | 1946-10-04 | 1948-12-21 | Monsato Chemical Company | Process of making tertiary amines |
| US2494355A (en) * | 1944-11-01 | 1950-01-10 | Us Rubber Co | Salts of aromatic dithiocarboxylic acids as fungicides |
| US2536750A (en) * | 1947-05-19 | 1951-01-02 | Pittsburgh Coke & Chemical Co | Organic mercury compounds and germicidal compositions thereof |
| US2627491A (en) * | 1950-07-15 | 1953-02-03 | Wyeth Corp | Penicillin salts of substituted alkylene diamines |
-
1951
- 1951-10-16 US US251634A patent/US2670376A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1757394A (en) * | 1926-07-08 | 1930-05-06 | Winthrop Chem Co Inc | Aminoalkylamino derivative of aromatic aminohydroxy or polyamino compounds |
| US2151149A (en) * | 1935-05-31 | 1939-03-21 | Rca Corp | Television apparatus |
| US2121619A (en) * | 1937-09-18 | 1938-06-21 | Du Pont | Preservation of rubber |
| US2494355A (en) * | 1944-11-01 | 1950-01-10 | Us Rubber Co | Salts of aromatic dithiocarboxylic acids as fungicides |
| US2430722A (en) * | 1946-04-25 | 1947-11-11 | Us Rubber Co | Derivatives of chlorinated quinones as fungicides |
| US2457048A (en) * | 1946-10-04 | 1948-12-21 | Monsato Chemical Company | Process of making tertiary amines |
| US2536750A (en) * | 1947-05-19 | 1951-01-02 | Pittsburgh Coke & Chemical Co | Organic mercury compounds and germicidal compositions thereof |
| US2627491A (en) * | 1950-07-15 | 1953-02-03 | Wyeth Corp | Penicillin salts of substituted alkylene diamines |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3153093A (en) * | 1961-11-22 | 1964-10-13 | Abbott Lab | Amino derivatives of nu-cyclopropylbenzylamines |
| US3923813A (en) * | 1969-12-19 | 1975-12-02 | Christiaens Sa A | Derivatives of 2-aminoindanes |
| US4209302A (en) * | 1979-05-10 | 1980-06-24 | Morton-Norwich Products, Inc. | Marker for petroleum fuels |
| US20060142387A1 (en) * | 2003-06-10 | 2006-06-29 | Rodolfo Cadilla | Chemical compounds |
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