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Allantoin Urocanic Acid Complexes

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AU 51426/79 A
Q~
111W. 11111&8___
3.6
MICROCOPY RESOLUTION TEST CHART
NAPfONAL BUREAU OF STANDARD -1963 -A

AUSTRALIA PATENT APPLICATION FORM (CONVENTION) Form 4
COMMONW EALTH OF AUSTRALIA
Pa ten ts A ct
14 26/79 30CT 979 1CONVENTION APPLIC FOR A PATENT
Insert full ()CARROLL PRODUCTS-INCORIPORATED
sdre() /W 
ofaplcants
Wood River Junction,
hereby apply for the grant of a Patent for an invention entitled
Insert title "ALLANTOIN UROCANIC ACID COMPLEXES"
which is described in the accompanying complete specification. This application is a convention
application and is based on the application or applications for a patent or patents or similar protection
made in the following country or countries on the following date or dates:
Insert i0 Ja o e No. 
country In ndon().. nur, 17228
basicapplication in on No. 
was made.
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date(s) of
appilcatIon(s), in on No. 
inseart
~,rnber of in on No. 
basic
application.
in on No. 
*YfOur address for service is care of ARTHUR S. CAVE CO., Patent and Trade Mark Attorneys,
1 Alfred Street, Sydney, New South Wales, Australia 2000.
Wg ,Insert date Dated this nd day of o. t.0b. e. r. 19 
FPorm signed.
Signature(s) (I 5 ARROLL PRODUCTS INCORPORATED,,of applicant(s).
,if a cmpanyAtre sto be xctdBy Is P tn
In a manner B t aetAtres
corde ARTHJJ R S. CAVE CO.
,()SaIf an
Th~ Commissioner of Patents,
C~MON WEALTH OF AUSTRALI-A
ARTHUR S. CAVE a CO.
ATENT AND TRADE MARK ATTORNEYS JAMES G. SIELY. F.I.P.A.A.
SYDNEY
Ak C.-2 K

AUSTRALIA PATENT DECLARATION FORM (CONVENTION) Form 8
COMMONWEALtH O01F AUSTRALIA
Patents Act'19S2
t~,cI~ARATI9N IN SUPPORT 01 A CONVENTION APPLICATION UNDER
~PALT XVI FOR A PATENT OR PATENT OF ADDITION
To be signed by the applicant(s) or in the case of a Company, to be 4
signed by a person authorised by the Company5 .42i/1
In support of the Convention application made for a patentofadtnfranivtoneild
(a Iset ite Urocariic Acid. Comlexes
of invention.
Insert full IWN aes..Gordon..Si ely., .Pa t 
name(s) of IW I) JmsGro tn
declarant(s).
(c)Insrtof A Ithu r 5 
ad(cs) o f Q
addresrn(s)of 1 Alfred Street, Sydney Cove, 2000
a do solemnly and sincerely declare as follows: 
*ptn
1. 1 am/we are the applicant(s) for the ptnpatent of addition.
o (OR, IN THE CASE OF AN APPLICATION BY A BODY CORPORATE.)
1. IamwearautorisdbyCarroll Products Incorporated
the applicant for the patent t aeti elrto
patent of addition t aeti elrto
on its behalf.
The basic, application(s) as definled by Section 141 of the Act was/were made in the following
a I,
country or cov..trses on the following date(s) namely:-
Insert in(d) 5 A. on(e) pA14Ary.,.79NO. 2~~a 
which bSebastian9 B. 'Mecca
walIs il in No. 
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0*00 basic application.
00006 In sert full 3. I am/we are the actual inventor(s) of the invention referred to in the basic application.
names of
applicnt~s)(OR, WHERE A PERSON OTHER THAN THE INVENTOR IS THE APPLICANT)
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names(s of
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address(es) of U. S.A
acu l. a
Inventor(s).
is/are the actual inventor(s) of the invention and the facts upon which I mWe entitled to make
the application are as follows: the Company is
Mk Set out how (k arroll Products Incorporated is the as C ne of
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derive(s) .t.room. .t 
from actual
Inventor(s)
assignee of
frthe atual The basic application(s) referred to in paragraph 2 of this Declaration was/were the first
lnventor(s). application(s) made in a Convention country in respect of the invention the subject of the application.
Attestation or
legalization
niot required. Decl&red at SYDNEY this 2nd day of October 19 79
To:
The Commissioner of Patents,2
COMMON4WEALTH OF AUSTRALIA 
ARTUR CVE Co (Signature Declarant)
PATENT AND TRADE MARK ATTORNEYSAES OR NSIEYFI.PA.A
SYQM4EY AE ODNSEYFIPAA

MISTRAL A
~z
(11) AU-A 1-51,426/79
(12) PATENT SPECIFICATION
ABSTrRACT
(19) AU
51,426/79
2289
17.7.80
C07D 233/88
A61K 7/44
(22) 3.10.79
(32) 10.1.79
(24) 10.1.79
(33) US
C07D 233/64 A61K 7/42
Allantoin urocanic acid complexes
Carroll Productis Inc.
Mecca, S.B.
1. An allantoin urocanic acid complex of the
formula[CH':N 40 3 [cH No wherein a and b are each
about 1.
120A
ND 26-4

AUSTRALIA.
PATENTS ACT 1952-1973
COMPLETE SPECIF ICAT ION
(ORIGINAL)
FOR OFFICE USE
51 426/79
50CT1979
Application Number:
Lodged:
Complete Specification Lodged:
Accepted:
Puliished:
Priority:
:Related Art:
TO BE COMPLETED oY APPLICANT
Name "of Applicant: CARROLL PRODUCTS INCORPORATED
Addret;s of Appl1icant: P.O. Box 66, Route 91, Wood River Junction,
RHODE ISLAND, UT.S.A.
~Acta~iInventor: Sebastian B. Mec6ca
Address for Service: ARTHUR S. CAVE CO., Patent Attorneys,
1 Alfred Street, SYDNEY COVE, 2000
Complete Specification for the invention entbitled
"ALLANTOIN UROCANIC ACID COMPLEXES"
,The following statement is a full description of this invention,
including -the best method of performing it known to me:-

~I f b E t a~E 11
1,426 m
BACKGROUND O5HE INVENTION
Allantoin is recognized as possessing soothing,
keratolytic, moisturizing and anti-irritant properties.
Allantoin salts and allantoin complexes are the subject
of U.S. Patents No. 3,107,252; 3,275,643; 3,290,323;
3,290,324; 3,305,557; 3,578,656; 3,632,596; 3,898,243;
3,927,021; 3,954,989; 3,970,748; and 3,970,756.
Urocanic acid is a metabolite derived from histidine.
-j It is found in human sweat and mammalian epidermis, and is
reported to have a role in protecting skin from ultraviolet
light. A description of urocanic acid, its properties
and uses is found in an article entitled Urocanic Acid
published by Ajinomoto Co., Inc. of Tokyo, Japan. This
article points out that urocanic acid may be effective as
a natural sun screen in cosmetics. It is known, however,
that alkaline salts, especially sodium salts of urocanic
acid exhibit a high solubility in water but that such
solutions undergo relatively rapid changes in color when
exposed to sunlight or heat. Urocanic acid in epidermis
is said to absorb 50% of ultraviolet radiation to which
it is exposed.
It is an object of this invention to provide novel
complexes of allantoin and urocanic acid which are not
sensitive to sunlight or heat and which may be used in a
variety of cosmetic formulations for beneficial effects.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to novel complexes of
allantoin and urocanic acid, and, more particularly to an
allantoin urocanic acid complex, an allantoin urocanic acid
salt complex and to cosmetic compositions containing these
complexes. The complexes of the invention may be depicted
as having <,he formulas:
[4H5N40a IC6 H6 N202 b (allantoin urocanic acid complex);
4 H N 0 3 ]a L6H6 N2 0Xlb (allantoin urocanate complex);
n
Z _w grein a and b are each about 1 and-" -fer to the number of
q mois of each component and X is a member selected from the
group con sisting of sodium, potassium and ammonium.
L3D The complexes are prepared by thoroughly mixing allantoin
with urocanic acid forming a semidry mass which is oven
dried to provide the desired complex. Alternatively,
allantoin and urocanic acid may be dissolved in an alkali
metal hydroxide solution, acidified to precipitate the
desired complex and oven dried. Allantoin and urocanic acid
are available commercially, and are used in such form in
preparing the complexes of this invention.
As mentioned, allantoin is known to possess soothing,
cleansing, tiealing, moisturizing, anti-irritant and skin
softening properties, and urocanic acid is recognized as
a natural ultraviolet absorber contained in human sweat.
Urocanic acid (iimidazole-4-acrylic acid), exists in trans
and cis isomeric forms. Natural urocanic acid consists
of the trans isomer with slight contamination of the cis
isomer. The trans isomer is slightly soluble in water,
slightly more soluble in boiling water, but almost insoluble
in organic solvents. The maximum absorption of ->traviolet
light by urocanic acid varies with the pH of solutions
of the acid, with maximum absorption of 28-290 mu
occurring with solutions having a pH of 7 to 
Allantoin and urocanic acid or alkali metal salts
or urocanic acid are preferably combined in a mol ratio of
about 1:1. In preferred embodiments of the invention,
all antoin and urocanic acid are combined in a mol ratio
of a out 1:1 to form allantoin urocanic acid complex.
LikeWise, allantoin and sodium, potassium or ammonium
urocanate are combined in a mol ratio of about 1:1 to form
r-4 an allantoin urocanic complex.
Elevated temperatures are required for formation of
the desired complexes. Thus, the reaction mixtures are
heated to temperatures of from about 1600 to 180 F. for
about 10 to 12 hours during formation of the complexes.
The complexes of this invention have the combined
attributes of the healing anti-irritant cleansing, emollient,
moisturizing and skin softening properties of allantoin,
and the ultraviolet absorption (sun screening) properties
of urocanic acid. Remarkably, the complexes of this
invention have been found to pose no problem of skin
irritation. Quantities effective to absorb about 100%
of the ultraviolet rays of the sun, and thus are signi-
ficantly more effective than conventional ultraviolet
absorbers. Also, the complexes surprisingly have been
found to be soluble in organic solvent including alcohol,
thus permitting the formation of topical compositions
with a urocanic acid content capable of maximum absorption
of ultraviolet light.
The complexes are useful in solution form or in
lotions or creams, where they demonstrate the ability to
maintain tissue moisture balance when the skin is exposed'
to ultraviolet rays of the sun. The complexes prevent
severe burning of the skin through absorption of ultraviolet
rays while allowing controlled tanning of the skin. At
the same time, the complexes permit the skin to remain
r- moisturized, supple and soft and reduce possible blemishes
resulting from exposure to the sun's rays. Generally, the
d" complexes are formulated in pharmaceutically acceptable
T-4
Scarriers at levels from 4 to 10 per cent, by weight, based
on the weight of the product, to form the desired sun
screening lotions and creams.
The following examples illustrate properties of the
complexes of this invention and suggested uses for the
complexes. The examples are illustrative only, and not
intended to limit the scope of the invention.
EXAMPLE 1
537 5. of allantoin is thoroughly mixed with 463 g.
of urocanic acid with vigorous trituration. 2 to 10% water
is added and thoroughly mixed forming a semidry mass which
is dried for 10 to 12 hours at 160° to 180 F. The complex
formed is soluble up to 0.4 to 0.6% in water, and soluble
in hot water, and analyzes allantoin 53% 5% and urocanic
acid 47% 
EXAMPLE 2
537 g. of allantoin and 463 g of urocanic acid is
dissolved in 3000 cc. of a 10% solution of sodium hydroxide.
The solution is acidified with 50% acetic acid to a pH
of 4.5 to 5 with constant mixing. The solution is allowed
to stand overnight in an ice bath, and allantoin urocanic
acid is removed by filtration. The allantoin urocanic
acid is washed with distilled water and dried at 1600to
180 F. for 10 to 12 hours forming a complex slightly
soluble in water and soluble in hot water. The complex
analyzes allantoin 20% 5% and urocanic acid 80% 
The example may be repeated using potassium hydroxide
or ammonium hydroxide in place of sodium hydroxide.
Infrared spectral analysis establishes that the allan-
toin urocanic acid complexes of this invention are
distinct chemical entities, and this fact is supported
by the physical and chemical properties of the complexes.
Additionally, aluminum derivatives of the allantoin urocanic
acid derivatives may be prepared by reacting allantoin
aluminum derivatives with urocanic acid.
The following formulations were made to demonstrate
the usefulness of allantoin urocanic acid complexes.
SUN SCREENING CREAM
INGREDIENTS
Ceraphyl 424
Isopropyl Myristate
Witconal APM
Promulgen D
Cetyl Alcohol
Lexemul 561
Myrj 52S
Span 65
Tegosept P
Escalol 507
Deionized Water
Germall
WEIGHT PER CENT
INGREDI.FNTS
Tegosept M
Sodium Benzoate
Sorb is tat
Sequestrene AA
Spectra Sorb UV-284
Urocanic Acid
Allantoin Pararn-inobenzoic Acid
Allantoin Urocanate
Triethanolamine
FD&C Yellow =1[5 
FD&C Yellow =11--6 
Perf\,rnie RSC jf8
WEIGHNT VER CENT
SUN SCREEN GEL
Snow White Petrolatum
Allantoin Paramino Benzoic Acid
Urocanic Acid
Allantoin Urocanate
Ozokerite
Spermwax
Snow White Petrolatum
Carnation Oil
Butyl Stearate
Dipiopylene Glycol Salicylate
Giv Tan F
Tegosept B
Tegosept P
Red 4A.17 (K7007) 0.06% in Corn Oil
Violet ff-2 (0701.4) 0.06% in Corn Oil
Perfume RSC 48~

SUNSCREEN CREAM
INGREDIENTS
Cer-aphyl 424
Isopropyl Myristate
Witconal APM
Promulgen D
Cetyl iAlcoho1
Lexemul 561
Myrj 52S
Span 65
Tegosept P
Escalol 507
Deionized Water
Allantoin Paraminobenzoic Acid
Germal 1
Tegosept M
Sodium Benzoate
Sorbistdt
Sequestrene AA
Spectrasorb UV-284
Allantoin Urocanate
Urocanic Acid (Ajimonto)
Trimethanolamine
Perfume RSC :118
W~EIGHT PER CENT

The claims defining the invention are as follows:
1. An allantoin urocanic acid complex of the formula
I 4 HN 403 a [C6H6N20]b wherein a and b are each about 1.
2. An allantoin urocanate complex of the formula
S~C4 H5 N4 3 a LCH6N 2lb wherein a and b are each
Sabout 1 and refer to the number of mols of each component
and X is a member selected from the group consisting of
-4 sodium, potassium an, ammonium.
3. An allantoin urocanic acid complex according
to claim 1 substantially as herein described with reference
to example 1.
4. An allantoin urocanate complex according to claim 2
substantially as herein described with reference to
example 2.
A pharmaceutical preparation comprising a complex
according to any one of the preceding claims, in admixture
with solid or liquid pharmaceutically acceptable carriers.
6. A process for producing complexes according to any one
of claims 1 to 4 substantially as herein described.
7. A method of preventing severe burning of skin exposed
to ultra-vioet light while allowing controlled tanning
of the skin which comprises applying to said skin a
pharmaceutical preparation as defined in claim 
wherein the ultra-violet light is absorbed by the urocanic
acid content of the preparation.
DATED this 2nd day of October, 1979.
CARROLL PRODUCTS INCORPORATED
By Its Patent Attorneys,
ARTHUR S. CAVE CO.

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