US3875301A - Useful tetraalkyl diamides in the treatment of poison ivy - Google Patents

Useful tetraalkyl diamides in the treatment of poison ivy Download PDF

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US3875301A
US3875301A US465527A US46552774A US3875301A US 3875301 A US3875301 A US 3875301A US 465527 A US465527 A US 465527A US 46552774 A US46552774 A US 46552774A US 3875301 A US3875301 A US 3875301A
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poison ivy
tetraalkyl
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aliphatic hydrocarbon
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Interx Research Corp
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides

Definitions

  • each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms
  • R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms.
  • the present invention relates to a method for alleviating the itching and clearing the rash on warmblooded animals. e.g.. humans. exposed to poison ivy. More particularly. the present invention is directed to a method for treating poison ivy through the use of certain tetraalkyl diamides.
  • US. Pat. No. 3.632.783 discloses the use of tetraalkyl diamides of this invention for obtaining relief from mosquito bites on humans.
  • these tetraalkyl diamides could be used in alleviating the dermatitis associated with poison ivy.
  • the irritant which causes the itching following a mosquito bite is not the irritant which causes the dermatitis following contact with the above-identified plants. responsible for poison ivy.
  • the compound dimethylacetamidc has been used in the treatment of the inflammation associated with arthritis.
  • this inflammation is not even remotely related to that observed in individuals suffering from "poison ivy.
  • the origin of inflammation in each case is totally unrelated. In fact. to date. it is questionable as to the origin of arthritis.
  • each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from I to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms
  • R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from O to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of from O to 22 carbon atoms.
  • the approach is novel from the standpoint that the therapeutic agent does not at all attempt to degrade urushiol but rather. it forms a molecular complex having properties which are different than the parent structure. and consequently. reduces its ability to illicit the typical dermatitis response noted after poison ivy contact.
  • the substituent *R includes any straight or branched chain or cyclo derivative within the definition of the same.
  • the substituent R is essentially a straight-chain moiety. though chains with a hydroxy substituent are also equivalent.
  • isomers of these acids can also be employed. for instance. iso-sebacic acid. isoglutaric. iso-adipic. etc.
  • tricarboxylic acids, such as tricarballie acid are equivalent. as are acids which include a hydroxy group. such as ricinoleic acid.
  • N.N.N.N-tetramethyl adipamide N.N.N.N-tetramethyl glutaramide N.N.N'.N'-tetramethyl sebacamide N.N.N'.N-tetramethyl succinamide
  • diamides which may also be used include:
  • the tetraalkyl diamides of this invention are preferably applied as a solution (normally, l95'/(, but preferably 25/( in water,
  • solution is meant to include a water-miscible alcohol solution, such as isoof adipic propyl alcohol or ethyl alcohol, or the alcohol may be used undiluted.
  • the solution is applied in any suitable manner, e.g., by spraying or swabbing the dermatitic area.
  • the tetraalkyl diamides of this invention may be applied in the form of any other topical pharmaceutical form, such as a powder, paste, salve, ointment, aerosol spray, etc.
  • Freon l4 carbon lctral'luoride lreon 3 l X (()etaflurocyelobutancl. Freon 1 l4 ((ryofluoraneJ. etc.
  • Formulation Number 4 Ointment N.N.N'.N-tetrameth)'l succinamide l Petrolatum USP t s EXAMPLE II (in Vivo Studies)
  • a topical aerosol formulation, in accordance with Formulation Number 3 of Example I above was prepared.
  • the concentration of tetramethylsuccinamide in the formulation was 5 percent.
  • the halogenated hydrocarbon propellant employed was a conventional propellant, *Freon ll-l2 (50/50). *A 50/50 mixture of Freon I1 and Freon 12.
  • the aerosol was applied to dermatitic areas resulting from poison ivy contact on human volunteers of both sexes. Within 24 to 36 hours following application, dramatic reduction in the dermatitis of each individual treated was observed.
  • the tetraalkyl diamide compounds of this invention are highly water soluble and a finite affinity for the organic phase. These characteristics permit dermal penetration without significant systemic absorption. in addition, the topical LD of these compounds is relatively high. For instance, the compound, N,N,N.N- tetramcthyl succinamide gave a topical LD of 2000 mg./Kg. when applied to denuded rabbits.
  • a method of reducing poison ivy dermatitis on a warm-blooded animal which comprises applying to the dermatitic area, an effective amount of a compound of the formula:
  • each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group olfrom I to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from I to (a carbon atoms. and wherein R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of l'r'om to 22 carbon atoms.
  • said propellant is a 50/50 mixture of triehlorotluoromethane and dichlorodil'luoromethane.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The relief from poison ivy on warm-blooded animals is obtained by applying to the surface of the affected area, a tetraalkyl diamide of the formula:

WHEREIN EACH R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms, and wherein R1 represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms.

Description

United States Patent [1 1 [111 3,875,301 Windheuser Apr. 1, 1975 USEFUL TETRAALKYL DIAMINES IN THE Primary Examiner-Albert T. Meyers TREATMENT OF POISON IVY [75] Inventor: John J. Windheuser, Lawrence,
Kans.
[73] Assignee: Interx Research Corporation,
Lawrence, Kans.
[22] Filed: Apr. 30, 1974 [21] Appl. No.: 465,527
[52] U.S. Cl 424/45, 424/320 [51] Int. Cl. A6lk 27/00, A611 23/00 [58] Field of Search 424/320, 45
[56] References Cited UNITED STATES PATENTS 3,288,794 11/1966 Kuceski 260/56] R 3,312,620 4/1967 Low et al..... 260/561 R 3,417,114 12/1968 Kuceski 260/557 3.632.783 1/1972 Stonis 424/320 Assistant ExaminerNorman A. Drezin' Attorney, Agent, or Firm-Charles N. Blitzer [57] ABSTRACT The relief from poison ivy on warm-blooded animals is obtained by applying to the surface of the affected area, a tetraalkyl diamide of the formula:
0 0 'R 11 11 /R R N-C-R -C-N R wherein each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms, and wherein R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms.
11 Claims, No Drawings USEFUL TETRAALKYI. DIAMINES IN THE TREATMENT OF POISON IVY BACKGROUND OF THE INVENTION 1. FIELD OF THE INVENTION The present invention relates to a method for alleviating the itching and clearing the rash on warmblooded animals. e.g.. humans. exposed to poison ivy. More particularly. the present invention is directed to a method for treating poison ivy through the use of certain tetraalkyl diamides. I I
2. DESCRIPTION OF THE PRIOR ART It is well known to those versed in the art and science of medicine that subsequent to exposure. either by direct contact or from the volatile oils of the plant Rhus (Toxicodendron L.) and other plants of the Rhus species (Anacardiaceae) an annoying dermatitis appears. This dermatitis takes the form of an itching rash which subsequently develops into a running itching area. It appears that the reaction is an allergic response to an irritant catechol compound known as urushiol. a volatile oil found in the above-identified plants. The chemical structure for urushiol can be found in Merck Index. p. 1098 (Eighth Ed.).
To date. numerous therapeutic formulations have evolved for the treatment of poison ivy. such as treatment with strong alkaline soaps. the use of astringents and drying agents. such as calamine. the use of topical application of anti-histamines. and the use of zirconium salts. However. none of the above therapeutic measures have been truly found to'be effective in treating the patient either prior to or following exposure to the poison ivy irritant. Moreover, none of the above measures are directed at the causative agent of the dermatitis associated with poison ivy.
US. Pat. No. 3.632.783 discloses the use of tetraalkyl diamides of this invention for obtaining relief from mosquito bites on humans. However. there is no disclosure or suggestion by the patentee to the effect that these tetraalkyl diamides could be used in alleviating the dermatitis associated with poison ivy. Moreover. the irritant which causes the itching following a mosquito bite is not the irritant which causes the dermatitis following contact with the above-identified plants. responsible for poison ivy.
The compound dimethylacetamidc has been used in the treatment of the inflammation associated with arthritis. However. this inflammation is not even remotely related to that observed in individuals suffering from "poison ivy. Obviously. the origin of inflammation in each case is totally unrelated. In fact. to date. it is questionable as to the origin of arthritis.
SUMMARY OF THE INVENTION It is the primary object of this invention to provide a new and novel approach to the treatment of the poison ivy dermatitis found on warm-blooded animals. e.g. humans by actually eancelling out the irritant effect produced by the compound known as urushiol.
The above object is obtained by applying to the dermatitic area of a patient afflicted with poison ivy. a tetraalkyl diamide of the formula:
wherein each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from I to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from 1 to 6 carbon atoms, and wherein R, represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from O to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of from O to 22 carbon atoms.
Specifically. it has now been found that the use of any one of the above-identified compounds significantly reduces the dermatitis associated with poison ivy. The reduction in the dermatitis is due to the interaction of the tetraalkyl diamide with urushiol to alter the physiological activity of the latter.
The approach is novel from the standpoint that the therapeutic agent does not at all attempt to degrade urushiol but rather. it forms a molecular complex having properties which are different than the parent structure. and consequently. reduces its ability to illicit the typical dermatitis response noted after poison ivy contact.
With respect to the above-identified generic formula. the following remarks for purposes of clarification are deemed pertinent. The substituent *R includes any straight or branched chain or cyclo derivative within the definition of the same. The substituent R, is essentially a straight-chain moiety. though chains with a hydroxy substituent are also equivalent.
Consequently. one may use a diamide of oxalic. malonic. succinic. glutarie. maleic. adipie. pimclic. suberic. azelaie. sebacic. undecanoic. dodecanoic. octadecylic. or eicosanoic acid. etc.. provided the total number of carbon atoms in the diamide do not exceed about 20. In addition. isomers of these acids can also be employed. for instance. iso-sebacic acid. isoglutaric. iso-adipic. etc. Moreover. tricarboxylic acids, such as tricarballie acid are equivalent. as are acids which include a hydroxy group. such as ricinoleic acid.
PREFERRED EMBODIMENTS OF THE INVENTION While all the compounds encompassed within the above generic formula are suitable for the purposes of this invention. the following are preferred:
N.N.N.N-tetramethyl adipamide N.N.N.N-tetramethyl glutaramide N.N.N'.N'-tetramethyl sebacamide N.N.N'.N-tetramethyl succinamide Other diamides which may also be used include:
N.N.N'.N'-tetrabutyldiamide of oxalic acid N.N.N.N-tetra-n-butyldiamide of malonie acid N.N-dibutynylamidc-N.N-diallylamide of malonic acid N.N-din-butylamide-N'.N'-diethylamide of succinic acid N.N-dimethylamide-N.N'-dibutylamide of succinic acid N.N.N'.N'-tetramethyldiamides of iso-glutaric acid N.N.N'.N-tetraallyldiamide of glutaric acid N.N-dimcthylamide-N.N-dibutylamide of glutaric acid N.N-di(methylethyl)-N.N'-dimethylamide of adipic acid N.N.N.N'-tetramethyldiamides of iso-adipie acid N,N-dimethylamide-N,N'-dibutylamide acid N,N-dimethyl-N,N'-dihcxyldiamide of pimelic acid N,N,N,N-tetraisopropyldiamide of azelaic acid N,N-dimethyl-N',N'-dihexyldiamide of azelaic acid N,N,N,N-tetraallyldiamide of azclaic acid N,N-di-n-butyl-N,N'-dihexylamide of sebacic acid N,N,N',N'-tetramethyldiamide of iso-sebacic acid N,N,N',N'-tetraisopropyldiamidc of brassylic acid The compounds of this invention may be prepared according to the established synthesis procedure set forth in US. Pat, No. 3,417,114 and/or US. Pat. No. 3,288,794, the subject matter of which, insofar as it pertains to the preparation of such compounds, is ineorporated herein by reference.
The tetraalkyl diamides of this invention are preferably applied as a solution (normally, l95'/(, but preferably 25/( in water, The term solution" is meant to include a water-miscible alcohol solution, such as isoof adipic propyl alcohol or ethyl alcohol, or the alcohol may be used undiluted. The solution is applied in any suitable manner, e.g., by spraying or swabbing the dermatitic area. Alternatively, the tetraalkyl diamides of this invention may be applied in the form of any other topical pharmaceutical form, such as a powder, paste, salve, ointment, aerosol spray, etc. These compounds can also be dissolved in a cosmetic base, a cream or oil, and added to other solutions or sprays normally applied to the skin, such as insect repellants, sun screen lotions, and ointments and creams normally used in the treatment of skin rashes and allergies, and in topical anesthetics used for the relief of pain and itching of sunburn. The skilled artisan concerned with the subject matter of this invention can easily prepare any of the above-mentioned conventional pharmaceutical dosage forms for topical application by simply referring to REMINGTONS PHARMACEUTICAL SCIENCES" (Fourteenth Edition), I970, pp, l46l-l762.
Normally. a single application brings immediate relief to the area treated; however, for stubborn cases, repeated application may be necessary.
Without further elaboration, it is believed that one of ordinary skill in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the specification and claims in any way whatsoever.
EXAMPLE I Set forth below are some illustrative topical formulations containing a selected tetraalkyldiamide coinpound of the instant invention.
Formulation Number I Solution N,N,N',N'-tetramethyl succinamide l 2571 Distilled water qs to 100% Procedure: Dissolve the tetramcthyl succinamidc in enough water to make 100%, Filter the solution. Apply to the effected area.
Formulation Number 2 Tincture N,N.N',N'-tetramethyl succinamide l Alcohol USP 5071 Water qs 10071 Procedure: Dissolve the tetramcthyl succinamide in the alcohol. Add sufficient water to make Filter and apply to affected area.
Formulation Number 3 Topical Aerosol N,N,N',N'-tetramethyl succinamide l 2571 Alcohol USP 5% lsopropylmyristate 57 *(onvenlional halogenated hydrocarbon propellant us (00% 0.2g. Freon ll ltrichlorol'uluromethane). Freon l2 Idichlorodil'luromelhane),
Freon l4 (carbon lctral'luoride lreon 3 l X (()etaflurocyelobutancl. Freon 1 l4 ((ryofluoraneJ. etc.
Procedure: Dissolve the tetramcthyl succinamide in the alcohol and isopropylmyristate. Add sufficient halogenated propellant and introduce into conventional aerosol containers either by pressure or by cold filling. Apply to affected area.
Formulation Number 4 Ointment N.N.N'.N-tetrameth)'l succinamide l Petrolatum USP t s EXAMPLE II (in Vivo Studies) A topical aerosol formulation, in accordance with Formulation Number 3 of Example I above was prepared. The concentration of tetramethylsuccinamide in the formulation was 5 percent. The halogenated hydrocarbon propellant employed was a conventional propellant, *Freon ll-l2 (50/50). *A 50/50 mixture of Freon I1 and Freon 12.
At 24 hour intervals, the aerosol was applied to dermatitic areas resulting from poison ivy contact on human volunteers of both sexes. Within 24 to 36 hours following application, dramatic reduction in the dermatitis of each individual treated was observed.
The tetraalkyl diamide compounds of this invention are highly water soluble and a finite affinity for the organic phase. These characteristics permit dermal penetration without significant systemic absorption. in addition, the topical LD of these compounds is relatively high. For instance, the compound, N,N,N.N- tetramcthyl succinamide gave a topical LD of 2000 mg./Kg. when applied to denuded rabbits.
From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions. Thus, such changes and-modifications are properly, equitably and intended to be, within the full range of equivalence for the following claims.
What I claim is:
l. A method of reducing poison ivy dermatitis on a warm-blooded animal, which comprises applying to the dermatitic area, an effective amount of a compound of the formula:
wherein each R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group olfrom I to 6 carbon atoms and an unsaturated aliphatic hydrocarbon group of from I to (a carbon atoms. and wherein R represents a member selected from the group consisting of a saturated aliphatic hydrocarbon group of from 0 to 22 carbon atoms and an unsaturated aliphatic hydrocarbon group of l'r'om to 22 carbon atoms.
whereby said compound forms a molecular complex with urushiol, the causative agent of said dermatitis. 2. The method of claim I, wherein said compound is: N.N.N.N '-tetramethyl adipamide. 3. The method ol claim I, wherein said compound is:
N.N.N',N'-tetramethylg|utaramide.
4. The method of claim I, wherein said compound is:
N.N,N.N-tetramethylsebacamide.
5. The method ol'claim I, wherein said compound is:
N N,N,N'-tetramethylsuccinamide.
6. The method of claim I, in which said compound is applied as a pharmaceutically acceptable topical preparation.
7. The method ol'claim 2, wherein said compound is applied as a water solution.
8. The method of claim 2, wherein said compound is applied as an alcohol solution.
9. The method of claim 2, wherein said compound is applied as an aqueous-alcoholic solution.
10. The method of claim 2, wherein said compound is applied as a halogenated hydrocarbon propellant solution.
11. The method of claim 10, wherein said propellant is a 50/50 mixture of triehlorotluoromethane and dichlorodil'luoromethane.
* a: q: a: :k
TINTTED STATES PATENT OFFICE QETTFTQATE ECTION Q Patent No. 3,875,301 Dated April 1, 1975 Invent (s) John J. Windheuser It is certified that error appears in the aboveidentified patent and that said Letters Patent are hereby corrected as shown below:
IN THE TITLE:
Delete "DIAMINES" and insert --DIAMIDES-.
" IN THE SPECIFICATION:
Column 3, the first line following the heading "Formulation Number 2 Tincture" delete "l"; delete "25%" and insert l 25% 0 Column 4, the first line following the heading "Formulation Number 3 Ibpical Aerosol" delete "l"; delete "25%" and insert l 25% ColuIm 4, the first line following the heading "Formulation Q Number 4 Ointment" delete "l"; delete "25%" and insert l 25% this itd an 0 fifth ay of August 1975 [SEAL] Arrest:
0 RUTH C. MASQN C. MARSHALL DANN Arresting Off 11'" (umml'ssium'r nt'lurcnls and Trudvmurks

Claims (11)

1. A METHOD OF REDUCING POISON IVY DERMATITIS ON A WARMBLOODED ANIMAL, WHICH COMPRISES APPLYING TO THE DERMATITIC AREA, AN EFFECTIVE AMOUNT OF A COMPOUND OF THE FORMULA
2. The method of claim 1, wherein said compound is: N,N,N'',N''-tetramethyl adipamide.
3. The method of claim 1, wherein said compound is: N,N,N'',N''-tetramethylglutaramide.
4. The method of claim 1, wherein said compound is: N,N,N'',N''-tetramethylsebacamide.
5. The method of claim 1, wherein said compound is: N,N,N'',N''-tetramethylsuccinamide.
6. The method of claim 1, in which said compound is applied as a pharmaceutically acceptable topical preparation.
7. The method of claim 2, wherein said compound is applied as a water solution.
8. The method of claim 2, wherein said compound is applied as an alcohol solution.
9. The method of claim 2, wherein said compound is applied as an aqueous-alcoholic solution.
10. The method of claim 2, wherein said compound is applied as a halogenated hydrocarbon propellant solution.
11. The method of claim 10, wherein said propellant is a 50/50 mixture of trichlorofluoromethane and dichlorodifluoromethane.
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Cited By (15)

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US5369108A (en) * 1991-10-04 1994-11-29 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
US5409908A (en) * 1993-10-20 1995-04-25 Vyrex Corporation Complexing urushiols
US5443847A (en) * 1993-07-15 1995-08-22 West; Philip W. Specific detoxification of urushiol with manganese salts
US5700811A (en) * 1991-10-04 1997-12-23 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and method of use thereof
US5767109A (en) * 1993-10-20 1998-06-16 Sanchez; Robert A. Complexing urushiols
WO2001010402A1 (en) * 1999-08-06 2001-02-15 Innovet Italia S.R.L. Use of n,n1-bis(2-hydroxyethyl)nonandiamide as a cosmetic agent
US6423746B1 (en) 1999-07-03 2002-07-23 The William M. Yarbrough Foundation Urushiol induced contact dermatitis and method of use
US6511990B1 (en) 1999-09-08 2003-01-28 Sloan-Kettering Institute For Cancer Research Class of cytodifferentiating agents and histone deacetylase inhibitors, and methods of use thereof
USRE38506E1 (en) 1991-10-04 2004-04-20 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
WO2004052358A1 (en) * 2002-12-04 2004-06-24 The William Yarbrough Foundation Urushiol induced contact dermatitis treatment and method of use
US20040131696A1 (en) * 2003-01-06 2004-07-08 Gilbert Buchalter Skin treatment for relief of itch
US20040266818A1 (en) * 2003-04-01 2004-12-30 Ronald Breslow Hydroxamic acid compounds and methods of use thereof
US20070203040A1 (en) * 2006-02-24 2007-08-30 Harry Reicherz Bar soap
US20080185113A1 (en) * 2007-01-29 2008-08-07 Ramon Valls Emulsions
USRE45335E1 (en) * 2004-04-01 2015-01-13 Tec Laboratories, Inc. Triple-action remedy for removing toxic oils from skin with simultaneous soothing and healing

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US3312620A (en) * 1964-12-21 1967-04-04 Shell Oil Co Amide lubricants
US3417114A (en) * 1965-07-20 1968-12-17 C P Hall Company Of Illinois Method of making amides from moisture and acid-gas containing esters
US3632783A (en) * 1969-05-27 1972-01-04 Hall Co C P Treatment of mosquito bites employing certain tetraalkyl diamides

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US3288794A (en) * 1962-09-12 1966-11-29 C P Hall Company Of Illinois Method of making amides of dimethylamine and piperazine
US3312620A (en) * 1964-12-21 1967-04-04 Shell Oil Co Amide lubricants
US3417114A (en) * 1965-07-20 1968-12-17 C P Hall Company Of Illinois Method of making amides from moisture and acid-gas containing esters
US3632783A (en) * 1969-05-27 1972-01-04 Hall Co C P Treatment of mosquito bites employing certain tetraalkyl diamides

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5932616A (en) * 1991-10-04 1999-08-03 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
EP0642509A4 (en) * 1991-10-04 1995-01-31 Sloan Kettering Inst Cancer Novel potent inducers of terminal differentiation and methods of use thereof.
EP0642509A1 (en) * 1991-10-04 1995-03-15 Sloan-Kettering Institute For Cancer Research Novel potent inducers of terminal differentiation and methods of use thereof
US5369108A (en) * 1991-10-04 1994-11-29 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
USRE38506E1 (en) 1991-10-04 2004-04-20 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
US6087367A (en) * 1991-10-04 2000-07-11 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and methods of use thereof
US5700811A (en) * 1991-10-04 1997-12-23 Sloan-Kettering Institute For Cancer Research Potent inducers of terminal differentiation and method of use thereof
US5443847A (en) * 1993-07-15 1995-08-22 West; Philip W. Specific detoxification of urushiol with manganese salts
US5767109A (en) * 1993-10-20 1998-06-16 Sanchez; Robert A. Complexing urushiols
WO1996032950A1 (en) * 1993-10-20 1996-10-24 Robert Sanchez Complexing urushiols
US5409908A (en) * 1993-10-20 1995-04-25 Vyrex Corporation Complexing urushiols
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