Title of Invention

NITRILE DERIVATIVES AS PERFUMING INGREDIENTS

Abstract The present invention concerns substituted benzylic nitriles substituted with lower linear alkyl or alkylene groups. These compounds are useful perfuming ingredients, and can impart odor notes of the floral-green type. The invention concerns also the perfuming compositions or perfumed articles associated with said compound.
Full Text Technical field
The present invention relates to the field of perfumery. More particularly, it
concerns substituted benzylic nitriles which are useful as perfuming ingredients, in
particular to impart odor notes of the floral-green type.
The present invention concerns also the use of said compounds in the perfumery
industry as well as the compositions or articles associated with said compounds.
Prior art
Amongst the compounds of formula (I), as defined below, a few are known. In
particular, all the compounds wherein the dotted line represents a double bond have been
previously described for various purposes such as chemical intermediates (for example:
butylidene-benzeneacetonitrile has been reported by S.I. Murahashi et al. in Synlett,
2000, 1016). However, none of the prior art documents disclosing a compound of formula
(I) reports or suggests any organoleptic properties of the invention's compounds, or any
use of said compound in the field of perfumery.
The compounds described in EP 682010 or in US 6069125 are the known
perfuming ingredients having the closest structure to the invention's compounds.
However, the invention's compounds not only differ from the prior art compounds in their
chemical structure but also in the organoleptic properties which are, in the case of the
prior art, of the marine or rosy-fruity(sweet) type. Nowhere in said two patents there is a
suggestion of any usefulness of the invention's compounds in the field of perfumery, and
even less of any organoleptic properties of the present compounds.
Description of the invention
We have now surprisingly discovered that a compound of formula



wherein R1 is a C1-4 linear alkyl group, and
a) the dotted line represents a double bond having a configuration E or Z or a mixture
thereof, and R2 is a hydrogen atom; or
b) the dotted line represents a single bond, and R2 is a C1-4 linear alkyl group;
can be used as perfuming ingredient, for instance to impart odor notes of the floral type.
According to a particular embodiment of the invention, R' represents a C2-C3
linear alkyl group, and in particular a n-propyl group.
According to any of the above mentioned embodiments, the compounds wherein
the dotted line represents a double bond are preferred, and in particular those having said
double bond in a configuration essentially Z, i.e. the Z isomer representing at least 90%
relative to the weight of the mixture.
Amongst said compounds of formula (I) those wherein the dotted line represents a
single bond and
i) R1 is a C3-4 linear alkyl group and R2 is a methyl group; or
ii) R1 is a C1-4 linear alkyl group and R2 is a C2-4 linear alkyl group
are new and are an object of the present invention.
Amongst the compounds of formula (I), one may cite in particular, and as non-
limiting example, (2Z)-2-phenyl-2-hexenenitrile. This compound has a substantive and
powerful floral, green-floral, odor with jasmine-muguet, lilac, herbal-lavender-rosemary
notes. The overall odor of this compound has a strong hexylcinnamic aldehyde
connotation (i.e. herbaceous-floral) and is also slightly green-geranium (e.g. of the-
diphenyl oxide type). The odor of the invention's compound has also bottom notes
presenting amyl salicilate and chocolate aspects.
More interesting, this compound can also display citrus or citronella notes
depending on the medium into which it is incorporated, as will be further illustrated in the
examples.

When compared to the prior art compound 2-phenyl-2-hexanenitrile (see
EP 682010), the invention's compound distinguishes by lacking, or by not possessing
significant, anethole/carvone-like undernotes, as well as by lacking, or by not possessing
significant, fruity (pineapple) and rosy notes which are characteristic of the prior art
compound. Said difference lends to (2Z)-2-phenyl-2-hexenenitrile and 2-phenyl-2-
hexanenitrile to be each suitable for different uses, i.e. to impart different organolpetic
impressions.
Another example of invention's compound is 2-(4-methylphenyl)hexanenitrile
which possesses an odor with floral-jasmine and geranium notes as well as nitrilic and
fruity notes. The overall scent is close to the fragrance of hexylcinnamic aldehyde.
Yet another example of invention's compound is 2-(4-ethylphenyl)pentanenitrile
which is characterized by a nice florale-jasminic and hyacinth note having also a
coumarine aspect. The bottom notes of this compound reminds of the odor of
hexylcinnamic aldehyde.
These last two compounds named do not have or are almost devoid of a particular
fruity or rosy connotation, to the contrary of 2-phenyl-2-hexanenitrile (see EP 682010)
Amongst the compounds of formula (I), (2Z)-2-phenyl-2-hexenenitrile and 2-(4-
methylphenyl)hexanenitrile are the preferred ones.
As mentioned above, the invention concerns the use of a compound of formula (I)
as perfuming ingredients. In other words it concerns a method to confer, enhance,
improve or modify the odor properties of a perfuming composition or of a perfumed
article, which method comprises adding to said composition or article an effective amount
of at least a compound of formula (I). By "use of a compound of formula (I)" it has to be
understood here also the use of any composition containing compound (I) and which can
be advantageously employed in perfumery industry as active ingredients.
Said compositions, which are in fact perfuming compositions that can be
advantageously employed as perfuming ingredient, are also an object of the present
invention.
Therefore, another object of the present invention is a perfuming composition
comprising:
i) as perfuming ingredient, at least one invention's compound as defined above;
ii) at least one ingredient selected from the group consisting of a perfumery carrier and a
perfumery base; and

iii) optionally at least one perfumery adjuvant.
By "perfumery carrier" we mean here a material which is practically neutral from
a perfumery point of view, i.e. that does not significantly alter the organoleptic properties
of perfuming ingredients. Said carrier may be a liquid or a solid.
As liquid carrier one may cite, as non-limiting examples, an emulsifying system,
i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A
detailed description of the nature and type of solvents commonly used in perfumery
cannot be exhaustive. However, one can cite as non-limiting examples solvents such as
dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-
ethoxyethoxy)-l-ethanol or ethyl citrate, which are the most commonly used.
As solid carrier one may cite, as non-limiting examples, absorbing gums or
polymers, or yet encapsulating materials. Examples of such materials, for example, may
comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides,
natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates,
polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as
H. Scherz, Hydrokolloids: Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel,
Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's VerlagGmbH
& Co., Hamburg, 1996. The encapsulation is a well known process to a person skilled in
the art, and may be performed, for instance, using techniques such as spray-drying,
agglomeration or yet extrusion; or consists of a coating encapsulation, including
coacervation and complex coacervation techniques.
Generally speaking, by "perfumery base" we mean here a composition comprising
at least one perfuming co-ingredient.
Said perfuming co-ingredient is not of the formula (I). Moreover, by "perfuming
co-ingredient" it is meant here a compound, which is used in perfuming preparation or
composition to impart a hedonic effect. In other words such a co-ingredient, to be
considered as being a perfuming one, must be recognized by a person skilled in the art as
being able to impart or modify in a positive or pleasant way the odor of a composition,
and not just as having an odor.
The nature and type of the perfuming co-ingredients present in the base do not
warrant a more detailed description here, which in any case would not be exhaustive, the
skilled person being able to select them on the basis of its general knowledge and
according to intended use or application and the desired organoleptic effect. In general

terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols,
aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or
sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients
can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in
reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969,
Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar
nature, as well as in the abundant patent literature in the field of perfumery. It is also
understood that said co-ingredients may also be compounds known to release in a
controlled manner various types of perfuming compounds.
Generally speaking, by "perfumery adjuvant" we mean here an ingredient capable
of imparting additional added benefit such as a color, a particular light resistance,
chemical stability, etc. A detailed description of the nature and type of adjuvant
commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that
said ingredients are well known to a person skilled in the art.
An invention's composition consisting of at least one compound of formula (I)
and at least one perfumery carrier represents a particular embodiment of the invention as
well as a perfuming composition comprising at least one compound of formula (I), at least
one perfumery carrier, at least one perfumery base, and optionally at least one perfumery
adjuvant.
It is useful to mention here that the possibility to have, in the compositions
mentioned above, more than one compound of formula (I) is important as it enables the
perfumer to prepare accords, perfumes, possessing the odor tonality of various
compounds of the invention, creating thus new tools for their work.
Its is also understood here that, unless otherwise indicated or described, any
mixture resulting directly from a chemical synthesis, e.g. without an adequate purification,
in which the compound of the invention would be involved as a starting, intermediate or
end-product could not be considered as a perfuming composition according to the
invention.
Furthermore, the invention's compound can also be advantageously used in all the
fields of modern perfumery to positively impart or modify the odor of a consumer product
into which said compound (I) is added. Consequently, a perfumed article comprising:
i) as perfuming ingredient, at least one compound of formula (I) as defined above; and
ii) a consumer product base,

is also an object of the present invention.
For the sake of clarity, it has to be mentioned that, by "consumer product base" we
mean here a consumer product which is compatible with perfuming ingredients. In other
words, a perfumed article according to the invention comprises the functional
formulation, as well as optionally additional benefit agents, corresponding to a consumer
product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least
one invention's compound.
The nature and type of the constituents of the consumer product do not warrant a
more detailed description here, which in any case would not be exhaustive, the skilled
person being able to select them on the basis of its general knowledge and according to
the nature and the desired effect of said product.
Examples of suitable consumer products include solid or liquid detergents and
fabric softeners as well as all the other articles common in perfumery, namely perfumes,
colognes or after-shave lotions, perfumed soaps, shower or bath salts, mousses, oils or
gels, hygiene products or hair care products such as shampoos, body-care products,
deodorants or antiperspirants, air fresheners and also cosmetic preparations. As detergents
there are intended applications such as detergent compositions or cleaning products for
washing up or for cleaning various surfaces, e.g. intended for textile, dish or hard-surface
treatment, whether they are intended for domestic or industrial use. Other perfumed
articles are fabric refreshers, ironing waters, papers, wipes or bleaches.
It has to be mentioned that the invention's compounds, due to their chemical
structure, which renders them quite resistant to many aggressive medium, are particularly
suitable for the preparation of perfuming composition for the functional perfumery.
The proportions in which the compounds according to the invention can be
incorporated into the various aforementioned articles or compositions vary within a wide
range of values. These values are dependent on the nature of the article to be perfumed
and on the desired organoleptic effect as well as the nature of the co-ingredients in a given
base when the compounds according to the invention are mixed with perfuming co-
ingredients, solvents or additives commonly used in the art.
For example, in the case of perfuming compositions, typical concentrations are in
the order of 0.001 % to 15 %by weight, or even more, of the compounds of the invention
based on the weight of the composition into which they are incorporated. Concentrations

lower than these, such as in the order of 0.01% to 10% by weight, can be used when these
compounds are incorporated into perfumed articles.
The compounds of formula (I) can be synthesized by a new and original process,
which is also an object of the present invention.
The invention's process is particularly useful for the preparation of a compound of
formula

wherein R3 and R4 represent, independently from each other, a hydrogen atom or a C1-4
linear alkyl or alkoxy group, and R5 represents a C1-8 linear or branched alkyl;
by reacting a nitrile of formula

wherein R3 and R4 have the meaning indicated above;
with an alcohol of formula R5 CH2OH, wherein R5 represents a C1-8 linear or branched
alkyl or alk-2-enyl;
in the presence of a catalytic system, said process being characterized in that the reaction
temparature is above 100°C and the catalytic system is a mixture comprising a base,
having a pKa above 13, and a complex selected from the group consisting of [RuCl2
(p-cym)]2 and [RuCl2(p-cym)(PPh3)], p-cym meaning p-cymene.
When R5, in formula R5CH2OH, represents an alkyl group then there is obtained a
compound of formula (II) wherein the dotted line represents a single bond. When R5, in

formula R5CH2OH, represents an alk-2-enyl group then there is obtained a compound of
formula (II) wherein the dotted line represents a double bond.
The complex is generally used in an amount ranging from 0.001 to 0.01 molar
equivalent relative to the amount of compound of formula (III).
Typical examples of base useful for the invention's process are KOH, NaOH or
DBU. Moreover, preferably, the base is present in an amount of about 5 to 15 molar
equivalents relative to the amount of the complex.
Furthermore, in said process the alcohol R5CH2OH may advantageously be used as
solvent, i.e. in a large excess compared to the amount of compound of formula (III).
Preferably, the compounds of formula (II) are those of formula (I).
The invention will now be described in further detail by way of the following
examples, wherein the abbreviations have the usual meaning in the art, the temperatures
are indicated in degrees centigrade (°C); the NMR spectral data were recorded in CDCl3
(if not stated otherwise) with a 400 or 100 MHz machine for 1H or respectively 13C, the
chemical displacements δ are indicated in ppm with respect to TMS as standard, the
coupling constants J are expressed in Hz.
Example 1
Synthesis of compounds of formula (I) according the invention's process
a) Preparation of (2Z)-2-phenyl-2-hexenenitrile
A 500 ml three necked flask equipped with a magnetic stirring bar and an argon inlet-
outlet, was charged with benzylnitrile (17.6 g, 150 mmol), crotyl alcohol (86.54 g,
1.2 mol, trans/cis mixture: 23/1), potassium hydroxide (420.9 mg, 7.5 mmol) and
[RuCl2(p-cym)]2 (229.8 mg, 0.38 mmol). The flask was then evacuated, back filled
with argon and heated at 100°C for 1.5 hour. When the reaction was terminated, the
reaction mixture was cooled and poured into water (500 ml), extracted with AcOEt
(3 x 100 ml). The organic phases were dried over anhydrous MgSO4, filtered and the
solvent was removed in vacuo. Distillation under reduced pressure gave the desired
nitrile with a yield of 45%.
1H-NMR analysis of this mixture showed also that nitrile was present as a mixture of
two diastereomers (Z/E = 95/5).

B.p.:121-123°C/5.4 mbar
13C NMR: 146.9 (d), 133.3 (s), 128.9 (d), 128.8 (d), 125.6 (d), 116.7 (s, CN), 116.1 (s),
34.1 (t), 22.0 (t), 13.7 (q).
lH NMR: 7.54-7.50 (m, 2H), 7.40-7.30 (m, 3H), 6.82 (t,J = 7.7, 1H), 2.56 (dt, J= 7.7,
7.2, 2H), 1.59 (sext, J= 7.2, 2H), 1.01 (t, J= 7.2, 3H).
b) Preparation of 2-(4-methylphenyl)hexanenitrile
A 500 ml three necked flask equipped with a magnetic stirring bar and an argon inlet-
outlet, was charged with 4-methylbenzylcyanide (19.73 g, 150 mmol), 1-propanol
(89.1 g, 1.2 mol), potassium hydroxide (423.5 mg, 7.5 mmol) and [RuCl2(p-cym)]2
(232.6 mg, 0.375 mmol). The flask was then evacuated, back filled with argon and
heated at 100°C for 1 hour. When the reaction was terminated, the reaction mixture
was cooled to room temperature and concentrated in vacuo. The residue was taken into
Et2O (500 ml) and washed with water (3 x 50 ml). The organic phase was dried over
anhydrous MgS04, filtered and the solvent was removed in vacuo. Distillation under
reduced pressure gave the desired nitrile with a yield of 70%.
B.p.: 105-106°C/1.3 mbar.
13C NMR: 137.7 (s), 133.1 (s), 129.7 (d), 127.1 (d), 121.1 (s, CN), 36.9 (d), 35.6 (t),
29.1 (t), 22.1 (t), 21.0 (q), 13.8 (q).
1H NMR: 7.19 (AB syst. JAB = 8.2, 4H), 3.72 (dd, J= 8.4, 6.4, 1H), 2.34 (s, 3H), 1.95-
1.78 (m, 2H), 1.52-1.29 (m, 4H), 0.89 (t, J= 7.2, 3H).
c) Preparation of 2-(4-ethylphenyl)pentanenitrile
Following the same procedure given in b), 4-ethylbenzylcyanide (5.08 g, 35 mmol),
1-propanol (21 ml, 280 mmol) were reacted with potassium hydroxide (99.1 mg,
1.75 mmol) and [RuCl2(p-cym)]2 (55.1 mg, 0.09 mmol) at 100°C for 1 h. Removal of
the solvent and distillation under reduced pressure gave the desired nitrile with a yield
of 51%.
B.p.:74-75°C/0.2 mbar.
13C NMR: 144.1 (s), 133.3 (s), 128.5 (d), 127.2 (d), 121.1 (s, CN), 37.9 (t), 36.8 (d),
28.5 (t), 20.3 (t), 15.5 (q), 13.4 (q).

1H NMR: 7.21 (AB syst. JAB = 8.4, 4H), 3.74 (dd, J = 8.4, 6.4, 1H), 2.64 (q, J = 7.7,
2H), 1.95-1.76 (m, 2H), 1.58-1.42 (m, 2H), 1.23 (t, J= 7.7, 3H), 0.95 (t,J =
7.2 Hz, 3H).
Example 2

Preparation of a perfuming composition
A perfuming composition for a "Savon de Marseille" was prepared by admixing the
following ingredients:








* in dipropyleneglycol
1) Origin: Firmenich SA, Geneva, Switzerland
2) Dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,l-b]furan; origin: Firmenich SA,
Geneva, Switzerland
3) 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyrane; origin
International Flavors & Fragrances, USA
4) Methyl dihydrojasmonate; origin: Firmenich SA, Geneva, Switzerland
5) Mixture of isomers of methylionones; origin: Firmenich SA, Geneva, Switzerland
6) l-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-l-ethanone; origin International
Flavors & Fragrances, USA

7) 3-(4-tert-Butylphenyl)-2-methylpropanal; origin: International Flavors &
Fragrances, USA
8) 3-Methyl-4/5-cyclopentadecen-1-one; origin: Firmenich SA, Geneva, Switzerland
9) 6,7-Epoxy-3,7-dimethyl-1,3-octadiene; origin: Firmenich SA, Geneva, Switzerland
10) 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; origin: Firmenich SA, Geneva,
Switzerland
11) 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol; origin:
Firmenich SA, Geneva, Switzerland
12) Methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate; origin: Firmenich SA,
Geneva, Switzerland
13) Propyl (S)-2-(1,1-dimethylpropoxy)propanoate; origin: Firmenich SA, Geneva,
Switzerland
14) 2-tert-Butyl-1-cyclohexyl acetate; origin: International Flavors & Fragrances, USA
The addition of 300 parts by weight of (2Z)-2-phenyl-2-hexenenitrile to the above-
described perfuming composition provided a new composition which had a fragrance
more functional, detergent-like. Moreover the new composition had a reinforced green-
citronella connotation.
Furthermore, when linen was washed with a detergent containing the new composition,
said linen after drying had a powerful salicylate note, of the floral-herbaceous type, which
was totally absent from a linen washed with a detergent containing the composition not
containing the invention's compound.
This connotation/note was lacking pineapple and rosy character.

Example 3
Preparation of a perfuming composition
A perfuming base for a soap was prepared by admixing the following ingredients:
Ingredient Parts by weight
Verdyl acetate 200




* in dipropyleneglycol
1) Dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,l-b]furan; origin: Firmenich SA,
Geneva, Switzerland
2) Origin: Firmenich SA, Geneva, Switzerland
3) 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyrane; origin
International Flavors & Fragrances, USA
4) Pentadecenolide; origin: Firmenich SA, Geneva, Switzerland
5) Mixture of isomers of methylionones; origin: Firmenich SA, Geneva, Switzerland
6) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; origin International
Flavors & Fragrances, USA
7) 3-(4-tert-Butylphenyl)-2-methylpropanal; origin: International Flavors &
Fragrances, USA
8) 4-(l,l-Dimethylethyl)-1-cyclohexyl acetate ; origin: Firmenich SA, Geneva,
Switzerland
9) 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol; origin:
Firmenich SA, Geneva, Switzerland
10) Perhydro-5,5,8aa-trimethyl-2a-trans-naphthalenyle acetate; origin: Firmenich SA,
Geneva, Switzerland
11) 3-(4-Tert-butylphenyl)-2-methylpropanal; origin: Givaudan-Roure SA, Vernier,
Switzerland
The addition of 150 parts by weight of (2Z)-2-phenyl-2-hexenenitrile to the above-
described perfuming base imparted to the fragrance of the latter a clear floral-jasmine and

salicylate connotation slightly green and cosmetic. This connation was lacking pineapple
and rosy character.

WE CLAIM:
1. A perfuming composition/perfumed article comprising a compound of the following formula:

wherein R1 is a C1-4 linear alkyl group, and
a) the dotted line represents a double bond having a configuration E or Z or a mixture thereof,
and R2 is a hydrogen atom; or
b) the dotted line represents a single bond, and R2 is a C1-4 linear alkyl group; in combination
with:
(i) at least one ingredient selected from the group consisting of a perfumery carrier and a
perfumery base; and
(ii) optionally at least one perfumery adjuvant, in the case of a perfuming composition;
or in combination with:
(iii) a consumer product base, in the case of perfumed article.
2. A perfuming composition/perfumed article, as claimed in claim 1, wherein:
in said formula (I) R1 represents C2-C3 linear alkyl group.
3. A perfuming composition/perfumed article, as claimed in claim 1 or 2, wherein:
in the said formula (I) the dotted line represents a double bond having a configuration Z.
4. A perfuming composition/perfumed article, as claimed in claim 3, wherein:
said compound is selected from the group consisting of (2Z)-2-phenyl-2-hexenenitrile and 2-(4-
methylphenyl) hexanenitrile.

5. A perfumed article as claimed in any of the preceding claims, wherein the consumer product
based is a solid or liquid detergent, a fabric softener, a perfume, a cologne or aftershave lotion, a
perfumed soap, a shower or bath salt, mousse, oil or gel, a hygiene product, a hair care product a
shampoo, a body-care product, a deodorant or antiperspirant, an air freshener, a cosmetic preparation, a
fabric refresher, an ironing water, a paper, a wipe or a bleach.
6. A compound of formula

wherein the dotted line represents a single bond and
i) R1 is a C3-4 linear alkyl group and R2 is a methyl group; or
ii) R1 is a C1-4 linear alkyl group and R2 is a C2-4 linear alkyl group.
7. The compound as claimed in claim 6, which is:
2-(4-methylphenyl)hexanenitrile or 2-(4-ethylphenyl)pentanenitrile.


The present invention concerns substituted benzylic nitriles substituted with lower
linear alkyl or alkylene groups. These compounds are useful perfuming ingredients, and
can impart odor notes of the floral-green type. The invention concerns also the perfuming
compositions or perfumed articles associated with said compound.

Documents:

00765-kol-2005-claims.pdf

00765-kol-2005-description complete.pdf

00765-kol-2005-form 1.pdf

00765-kol-2005-form 2.pdf

00765-kol-2005-form 3.pdf

00765-kol-2005-form 5.pdf

765-KOL-2005-ABSTRACT.pdf

765-kol-2005-assignment.pdf

765-KOL-2005-CLAIMS 1.1.pdf

765-kol-2005-correspondence.pdf

765-KOL-2005-DESCRIPTION (COMPLETE) 1.1.pdf

765-KOL-2005-EXAMINATION REPORT REPLY RECIEVED.pdf

765-kol-2005-examination report1.1.pdf

765-KOL-2005-FORM 1 1.1.pdf

765-kol-2005-form 18.pdf

765-KOL-2005-FORM 2 1.1.pdf

765-kol-2005-form 3.pdf

765-kol-2005-form 5.pdf

765-KOL-2005-FORM-27.pdf

765-kol-2005-gpa.pdf

765-KOL-2005-GRANTED CLAIMS1.1.pdf

765-kol-2005-granted-abstract.pdf

765-kol-2005-granted-description (complete).pdf

765-kol-2005-granted-form 1.pdf

765-kol-2005-granted-form 2.pdf

765-kol-2005-granted-specification.pdf

765-KOL-2005-OTHER PATENT DOCUMENT.pdf

765-kol-2005-others.pdf

765-kol-2005-reply to examination report.pdf

765-kol-2005-translated copy of priority document.pdf


Patent Number 250180
Indian Patent Application Number 765/KOL/2005
PG Journal Number 50/2011
Publication Date 16-Dec-2011
Grant Date 14-Dec-2011
Date of Filing 22-Aug-2005
Name of Patentee FIRMENICH SA
Applicant Address 1, ROUTE DES JEUNES, P.O. BOX 239 1211 GENEVA 8
Inventors:
# Inventor's Name Inventor's Address
1 SAUDAN LIONEL 36, RUE PREVOST-MARTIN 1205 GENEVA
2 WYSS PATRICK RUE LAMARTINE 18 1203 GENEVA
PCT International Classification Number C07C 255/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 PCT/IB2004/03031 2004-09-16 IB