Title of Invention

PROCESS FOR PRODUCINIG (Z)-1-PHENYL-1 DIETHYLAMINO CARBONYL-2-AMINOMETHYLCYCLOPROPANE HYDROCHLORIDE

Abstract A process for producing (Z)-l-phenyl-l-diethylaminocarbonyl-2- aminomethylcyclopropane or hydrochloride thereof, which comprises a step of reacting (Z)-l-phenyl-l-diethylaminocarbonyl-2- phthalimidomethylcyclopropane by contacting said compound with an aqueous methylamine solution having a concentration of from 1 to 25% by weight to obtain (Z)-l-phenyl-1-diethy laminocarbonyl-2- aminomethylcyclopropane, wherein the amount of methylamine is 4 to 20 gram equivalent per one gram equivalent of (Z)-1-phenyl-1- diethylaminocarbonyl-2-phthalimidomethylcyclopropane and the reaction temperature is 0 to 100°C.
Full Text PROCESS FOR PRODUCING (Z)-1-PHENYL-1-DIETHYLAMINOCARBONYL-2-
AMINOMETHYLCYCLOPROPANE HYDROCHLORIDE
FIELD OF THE INVENTION
The present invention relates to a process for producing
(Z)-l-phenyI-l-diethylaniinocarbonyl-2-aminomethylcyclopropane hydrochloride useful as an
antidepressant.
BACKGROUND OF THE INVENTION
(Z)-l-Phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride is
known as an antidepressant having an activity of serotonin-noradrenahn reuptake inhibitor.
As one of most effective methods for producing
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride, disclosed is
a process represented by the following scheme wherein (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane is treated by 40% aqueous solution of methylamine to
deprotect the phthalimide group and then converted to a hydrochloride thereof by an ethanol
solution of hydrogen chloride (refer to EP0200638A).

The above-mentioned process has problems that, when
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane is treated by 40%
aqueous solution of methylamine, by-produced N,N'-dimethylphthalamide precipitates out in a
reactant mixture forming a dispersed state, thereby disturbing smooth extraction processing.
Furthermore, the process applies an ethanol solution of hydrogen chloride in the step to
obtain hydrochloride salt; but since ethanol has too high solubility for
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride, the solubility

must be controlled by adding ethers such as diethyl ether or diisopropyl ether. However,
addition of ethers having high ignitability causes problems of safety in industrial applications.
SUMMARY OF THE INVENTIQN
The present invention intends to solve the above problems and to provide a simple and
safe process for producing (Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane
hydrochloride with high quality and yield.
After having diligently studied to solve the above problems, the present inventors have
achieved the present invention.
Namely, the invention has the following aspects.
A process for producing (Z)-l-phenyl-l-diethylaminocarbonyl-2-
aminomethylcyclopropane or hydrochloride thereof, which comprises a step of reacting
(Z)-l-phenyl-l-diethylaniinocarbonyl-2-phthalimidomethylcyclopropane by contacting said
compound with an aqu(JOus methylamine solution having a concentration of from 1 to 25% by
weight to obtain (Z)-l-phenyl-l-diethylandnocarbonyl-2-aniinomethylcyclopropane.
The process according to , wherein the concentration of the aqueous methylamine
solution is from 10 to 25% by weight.
The process according to or , wherein the amount of methylamine is 4 to 20
gram equivalent per one gram equivalent of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane.
The process according to any of to , wherein the contact is carried out in the
co-presence of an organic solvent.
The process ao^ording to , wherein the organic solvent is the one comprising
toluene.
The process accoTding to , wherein the organic solvent is the one consisting
essentially of toluene.
The process aax)rding to any of to , which further comprises a step contacting
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane with hydrogen chloride in
an organic solvent comprising ethyl acetate and isopropyl alcohol.
The process according to , wherein the organic solvent is the one consisting
essentially of ethyl acetate and isopropyl alcohol.
The process according to , wherein weight ratio of ethyl acetate to isopropyl
alcohol is 3 - 20 to 1.
The process according to , wherein weight ratio of ethyl acetate to isopropyl
alcohol is 3 - 20 to 1.
DESCRIFnON OF PREFERRED EMBODIMENTS
The present invention is explained in detail as follows.
The present invention is a process for producing
(Z)-l-phenyl-l-diethylaminocaibonyl-2-aniinomethylcyclopropane or hydrochloride thereof
wherein the process includes a step of contacting (Z)-l-phenyl-l-diethylaininocarbonyl-2-
phthalimidomethylcyclopropane by contacting said compound with an aqueous solution of
methylamine having a roncentration of 25% by weight or less,
and is also a process for producing
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride wherein the
process, succeeding to the step mentioned above, further includes a step of contacting
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane obtained with hydrogen
chloride in a solvent.
(Z)-1-Phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane, which is a
raw material in the prej>ent invention, is the known compound and can be produced, for example,
by a process described in EP0200638A.
It is essentially necessary for the process of the present invention to set a concentration
of the aqueous solution of methylamine in the range of 1 to 25% by weight, i.e. lower than 40%
by weight applied in the conventional art, and preferably 10 to 25% by weight, and more
preferably 14 to 25% by weight.
If the concentration of the aqueous solution of methylamine is higher than 25% by
weight, by-produced N,N'-dimethylphthalamide could precipitate in a reaction system with
causing a dispersed state and hindering smooth extraction operation. If the concentration is
lower than 1% by wei^^t, the reaction becomes unpractical because the reaction rate is
significantly reduced.
The concentration of the aqueous solution of methylamine may easily be controlled by
adding water in an on-going reaction system applied with a conunercially available aqueous
solution of methylamine having 40% by weight.
The amount of methylamine contained in the aqueous solution of methylamine is
necessary at least 2 gram equivalent or more per 1 gram equivalent of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane, in view of reaction
rate and volimie efficiency, preferably 4 to 20 gram equivalent, and more preferably 6 to 12
gram equivalent. Therefore, the aqueous solution of methylamine having the above-mentioned
concentration may be used in an amount to make the amount of the methylamine substantially
contained in the reaction system within the above-mentioned equivalent ranges.
The reaction of the present invention may be carried out solely in the aqueous solution
of methylamine, and may also be carried out in the co-presence of an organic solvent. From
the practical point of view, it is preferably carried out in the co-presence of the orgaiuc solvent
used for extraction operation after the reaction. The organic solvent is preferably the one
immiscible with water and un-reacted with methylamine. Examples thereof include aromatic
hydrocarbon solvents s;uch as toluene, and the tike; halogenated-aromatic hydrocarbon solvents
such as monochlorobeinzene, dichlorobenzene, and the like; saturated hydrocarbon solvents such
as hexane, heptane, and the like. These may be used alone or as a mixture of two or more
kinds thereof.
When the reaction is carried out in the co-presence of an organic solvent, the ratio of the
organic solvent to the aqueous solution of methylamine, under consideration of productivity
(volume efficiency), is preferably 0.5 to 5 in terms of a weight ratio of organic solvent/aqueous
solution of methylamine, and preferably 1 to 2.
The reaction temperature is usually 0 to 100°C, and preferably 10 to 100°C. The
reaction time is usually 2 to 30 hours.
Since by-produced N,N'-dimethylphthalamide is present under dissolved condition in a
water layer after the completion of the reaction, when the reaction is conducted in the
co-presence of an organic solvent, N,N'-dimethylphthalamide may easUy be removed by
leaving the reactant mixture settled as itself and then removing a water layer by a phase
separating operation. 'When an organic solvent is not used in the reaction, the reactant mixture
may be preferably extracted with the organic solvent and left settled, and then the resultmg water
layer is subjected to phaise separation. Since (Z)-l-phenyl-l-diethylaminocarbonyl-2-
aminomethylcyclopropane is dissolved in the organic layer,
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane may be isolated, if
necessary, by washing wiih water, drying, and concentrating.
Thus obtained (Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane may
be converted to a hydrochloride thereof by contacting said compound with hydrogen chloride in
an organic solvent including ethyl acetate and isopropyl alcohol. As the organic solvent, an
organic solvent consisting essentially of ethyl acetate and isopropyl alcohol is usually used.
The ratio of ethyl acetate to isopropyl alcohol in the organic solvent, in view of the
recovery rate of the intended compound and of the quality of the obtained crystals, is preferably
3 to 20 in terms of ethyl acetate/isopropyl alcohol (weight ratio), and more preferably 5 to 10.
From the view point of operabihty of suspension containing crystals of the intended
compound and a yield thereof, the amount of the solvent in terms of the total amount of ethyl
acetate and isopropyl alcohol is preferably 2 to 10 kg per 1 kg of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane, more preferably 3 to
7 kg.
The form of hydrogen chloride to be used is not limited, and hydrogen chloride may be
contacted with (Z)-l-phenyl-l-diethylaminocaTbonyl-2-phthalimidomethylcyclopropane by
being introduced in a gas state or being added as a solution dissolved in the solvent used in the
reaction. It is preferresd that hydrogen chloride is used as a solution of ethyl acetate, particularly
4 normal solution thereof because of easiness of commercial availability, easiness for
quantification, and good operability.
When being used as a solution of ethyl acetate, ethyl acetate contained in the solution is
counted as a part of ethyl acetate used in the reaction solvent.
The amount of hydrogen chloride, in view of the yield of the intended compound, is
preferably 1 to 2 gram equivalent per 1 gram equivalent of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane, and more preferably
1.1 to 1.3 gram equivalent.
(Z)-l-Phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride can
be precipitated by contai:toig with hydrogen chloride, and crystals of
(Z)-l-phenyl-l-diethylairninocarbonyl-2-aniinomethylcyclopropane hydrochloride can be
isolated by collection of crystals with filtration after stirred preferably at room temperature for 1
to 3 hours, preferably further by washing with ethyl acetate followed by drying.
The present invention will be explained in more detail according to Examples. The
present invention should not be limited thereto.
Referential Example 1: Production of 2-oxo-l-phenyl-3-oxabicyclo[3.1.0]hexane
In a mixed solution of toluene (26.0 kg) and N,N'-dimethylimidazolidinone (94.9 kg),
60% sodium hydride (27.2 kg; 683 mol) was added, and phenylacetoiutiile (40.2 kg, 343 mol)
was subsequentiy added dropwise thereto at 10 to 20°C. After the resulting mixture was stirred
for 2 hours, a mixture of epichlorohydrin (31.7 kg, 343 mol) and toluene (26.0 kg) was added
dropwise thereto at 10 to 20°C and then stirred. After confirming the disappearance of the raw
material, methanol (22.0 kg) and water (120.6 kg) were added therein to be subjected to washing
and phase separation.
24% Aqueous solution of potassium hydroxide (159.1 kg) and tetrabutylammonium
suliate (1.1 kg) was addtxl to the organic layer obtained, and the mixture was heated and
refluxed. After cooling down, the organic phase was removed by a phase separation.
Toluene (69.6 kg) and 35% hydrochloric add (78.7 kg)were further added to the aqueous phase,
and then the mixture was stirred at 60 to 70°C for 2 hours. After coohng down the mixture and
subjecting to a phase separation, an organic layer was further washed twice with 8% aqueous
sodium hydrogen carbonate solution and twice with water. The organic layer obtained was
concentrated under a reduced pressure to obtain 40.7 kg of the titled compound in a form of
hght-yellow oily substance, \leld was 68.1%.
The obtained oily substance of 2-oxo-l-phenyl-3-oxabicyclo[3.1.0]hexane was cooled
to transform to crystals.
Referential Example 2: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
hydroxymethylcyclopropane
After cooling a mixed solution of diethylamine (8.1 kg, 111 mol) and tetrahydrofuran
(33.2 kg) down to -75°C, 17% n-butyllithium-hexane solution (40.4 kg, 108 mol) was added
dropwise into the above mixture and then stirred for 1 hour. Thereafter, a solution of
2-oxo-l-phenyl-3-oxabicyclo[3.1.0]hexane(12.4 kg, 71.2 mol) dissolved with tetrahydrofuran
(10.4 kg) added dropwise into the mixture and then the resulting mixtiu-e was stirred at -60 to
-78°C. After completion of the reaction, the reacted liquid was added dropwise into 20%
aqueous solution of ammonium chloride (43.2 kg). After subjecting to phase separation, the
organic layer was concentrated by about 40% by weight under a reduced pressure. Toluene
(43.1 kg) was added to Ihe concentrated residue, and then the added mixture was washed twice
with water. The organic layer obtained was concentrated under a reduced pressure to obtain
11.5 kg of light-yeDow oUy substance as the titled compound. Yield is 66.8%.
The obtained oily substance of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
hydroxymethylcyclopropane was crystallized with a mixed solvent of ethyl acetate and
n-heptane to obtain Ught yellow crystals.
Referential Example 3 : Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
chloromethylcycloprop;ane
After dissolving (Z)-l-phenyl-l-diethylaminocarbonyl-2-hydroxymethylcyclopropane

(19.5 kg, 78.8 mol) with chloroform (68.9kg), thionyl chloride (10.3 kg, 86.6 mol) was added
dropwise to the above ijolution at 10 to 20°C and then the mixture was stirred for 2 hours.
After finishing the reaction, toluene (50.6 kg) was added thereto and then the added mixture was
concentrated under a reduced pressure. After toluene (67,6 kg) was added to the concentrated
residue, the resulting mixture was washed once with water, once with 8% aqueous sodium
hydrogen carbonate solution and further once with water. The obtained organic layer was
concentrated under a reduced pressure to obtain 20.6 kg of the titled compound in a form of
light-yellow oily substance. Yield was 96.7%.
Referential Example 4: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane
After heating a mixture of potassium phthahmide (16.7kg, 90.2 mol) and
N,N-dimethylformamide (81.4 kg) up to at 50°C, a solution of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-chloromethylcyclopropane (19.1 kg, 71.9 mol)
dissolved with N,N-dimethylfonnamide (9.0 kg) was added dropwise to the above mixture and
then the added mixture was stirred for 2 hours. After coohng down to 20°C, seed crystals of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-phthalimidomethylcyclopropane was seeded into the
resulting mixture, and then the inoculated mixture was stirred for 2 hours; further added
dropwise with water (57.4 kg), stirred for 1 hour, and then filtered to collect crystals. The
crystals were washed with water (50.0 kg), and then dried to obtain 25.0 kg of the titled
compound in a form of white crystals, \leld was 92.3%.
Example 1: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane
hydrochloride (substantial concentration of aqueous methylamine solution: 21% by weight)
Into a mixture of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane (18.2 kg, 48.4 mol), water (35.0 kg), and toluene (79.0 kg),
40% by weight aqueous monomethylamine solution (37.7 kg, 485 mol; the concentration of the
solution finally resulted in 21% by weight aqueous monomethylamine solution by combining

the amount of the water mentioned above) was added dropwise and stirred at 20°C for 20 hours.
After phase-separating the resultant reaction mixture, a water layer was extracted twice with
toluene. The organic layers obtained were mixed and dried with anhydrous magnesium sulfate,
and then filtrated and concentrated under a reduced pressure. To the solution of concentrated
residue added with ethyl acetate (67.1 kg) and isopropyl alcohol (9.0 kg), 4N-hydrogen
chloride-ethyl acetate (12.5 kg, 55.9 mol) was added dropwise. Crystals obtained were
collected by filtration, thien washed with ethyl acetate, and dried to obtain white powders of
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride (11.9 kg).
Yield was 86.9%.
Physical Properties : IH-NMR (D20,400MHz) 6:0.87 (3H, t, J=7.0Hz), 1.08 (3H, t, J=7.0Hz),
1.72-1.84 (3H, m), 2.43 (IH, m), 3.25-3.44 (4H, m), 3.71 (IH, m), 7.13-7.28 (5H, m), 8.80 (3H,
br-s)
Example 2: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane
hydrochloride (substantial concentration of the aqueous methylamine solution: 15% by weight)
Into a mixture of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane (3 g, 0.008 mol), toluene (15 ml), and water (10.3 g), 40% by
weight aqueous monomethylamine solution (6.20 g, 0.080 mol; the concentration of the solution
finally resulted in 15% by weight aqueous monomethylamine solution by combining the
amount of the water mentioned above) was added dropwise and stirred at 20°C for 18 hours;
yield determined with high-performance liquid chromatography (hereinafter, referred to as LC
quantified value) was 92.1%, and un-reacted raw material was remained.
Example 3 : Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane
hydrochloride (substantiial concentration of the aqueous methylamine solution: 10% by weight)
The experiment was carried out in the same manner as in Example 2 except that the
amount of water was 18.6 g. The LC quantified value was 88.0%, un-reacted raw material was
remained, and the reaction rate tended to delay in comparison with that of Example 2.
Example 4: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-ammomethylcyclopropane
hydrochloride (substantial concentration of the aqueous methylamine solution: 14.5% by
weight)
Into a mixture of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane (16.7 kg, 44.4 mol), water (36.1 kg), and toluene (72.3 kg),
40% by weight aqueous methylamine solution (20.7 kg, 266 mol; the concentration of the
solution finally resulted in 14.5% by weight aqueous methylamine solution by combining the
amount of the water mentioned above) was added dropwise and stirred at 40°C for 4 hours.
After phase-separating the resultant reaction mixture, a water layer was extracted twice with
toluene. The organic layers obtained were mixed and dried with anhydrous magnesium sulfate,
and then filtrated and oancentrated under a reduced pressure. To the solution of concentrated
residue added with ethyl acetate (64.0 kg) and isopropyl alcohol (8.5 kg), 4N-hydrogen
chloride-ethyl acetate (11.0 kg, 46.2 mol) was added dropwise. Crystals obtained were
collected by filtration, then washed with ethyl acetate, and dried to obtain white powders of
(Z)-l-phenyl-l-diethyl;aminocarbonyl-2-aminomethylcyclopropane hydrochloride (10.9 kg).
Yield was 88.2%.
Comparative Example 1: Production of (Z)-l-phenyl-l-diethylaniinocarbonyl-2-
aminomethylcyclopropane hydrochloride (substantial concentration of the aqueous
methylamine solution: 40% by weight)
The experiment was carried out in the same manner as in Example 2 except that no
water was added; 18 hours was required until the raw material nearly disappeared. The reaction
system was thick at the beginning, and left in a slurry state until the end of reaction.
Comparative Example 2: Production of (Z)-l-phenyl-l-diethylaminocarbonyl-2-
aminomethylcyclopropane hydrochloride (substantial concentration of the aqueous
methylamine solution: 27% by weight)

The experiment was carried out in the same manner as in Example 2 except that water
was used in an amount of 3 g. The reaction proceeded as nearly same as in Comparative
Example 1, and the reaction system was left in a slurry state by the end of reaction.
The process of the present invention allows to remove by-produced
N,N'-dimethylphthalamide with a simple operation such as phase separation of water layer,
thereby has advantages compared to the conventional processes which require troublesome
procedures such as extraction from a suspension.
Furthermore, in the process of the present invention, using a mixed solvent of ethyl
acetate and isopropyl alcohol in the step of converting (Z)-l-phenyl-l-diethylaminocarbonyl-2-
aminomethylcyclopropane to a hydrochloride thereof allows to obtain
(Z)-l-phenyl-l-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride in high
quality and high yield, thereby the process of the invention is more highly practical than the
conventional process which requires un-safe solvent such as ether or the like.

We Claim:
1. A process for producing (Z)-l-phenyl-l-diethylaniinocarbonyl-2-
aminomethylcyclopropane or hydrochloride thereof, which
comprises a step of reacting (Z)-l-phenyl-1-diethylaminocarbonyl-
2-phthalimidomethylcyclopropane by contacting said compound
with an aqueous methylamine solution having a concentration of
from 1 to 25% by weight to obtain (Z)-1-phenyl-1-
diethylaminocarbonyl-2-aminomethylcyclopropane, wherein the
amount of methylamine is 4 to 20 gram equivalent per one gram
equivalent of (Z)-l-phenyl-1-di ethylaminocarbonyl-2-
phthalimidomethylcyclopropane and the reaction temperature is 0
to 100°C.
2. The process as claimed in claim 1, wherein the concentration of the
aqueous methylamine solution is from 10 to 25% by weight.
3. The process as claimed in claim 1, wherein the contact is carried
out in the co-presence of an organic solvent.
4. The process as claimed in claim 3, wherein the organic solvent is
the one comprising toluene.
5. The process as claimed in claim 1, which further comprises a step
contacting (Z)-1 -phenyl-1 -diethylaminocarbonyl-2-
aminomethylcyclopropane with hydrogen chloride in an organic
solvent comprising ethyl acetate and isopropyl alcohol.
6. The process as claimed in claim 5, wherein the organic solvent is
the one consisting essentially of ethyl acetate and isopropyl
alcohol.
7. The process as claimed in claim 6, wherein weight ratio of ethyl
acetate to isopropyl alcohol is 3-20 to 1.


A process for producing (Z)-l-phenyl-l-diethylaminocarbonyl-2-
aminomethylcyclopropane or hydrochloride thereof, which comprises a step
of reacting (Z)-l-phenyl-l-diethylaminocarbonyl-2-
phthalimidomethylcyclopropane by contacting said compound with an
aqueous methylamine solution having a concentration of from 1 to 25% by
weight to obtain (Z)-l-phenyl-1-diethy laminocarbonyl-2-
aminomethylcyclopropane, wherein the amount of methylamine is 4 to 20
gram equivalent per one gram equivalent of (Z)-1-phenyl-1-
diethylaminocarbonyl-2-phthalimidomethylcyclopropane and the reaction
temperature is 0 to 100°C.

Documents:

03750-kolnp-2006-abstract.pdf

03750-kolnp-2006-claims.pdf

03750-kolnp-2006-correspondence others-1.1.pdf

03750-kolnp-2006-correspondence others.pdf

03750-kolnp-2006-correspondence-1.2.pdf

03750-kolnp-2006-correspondence-1.3.pdf

03750-kolnp-2006-description(complete).pdf

03750-kolnp-2006-form-1.pdf

03750-kolnp-2006-form-18.pdf

03750-kolnp-2006-form-2.pdf

03750-kolnp-2006-form-26.pdf

03750-kolnp-2006-form-3.pdf

03750-kolnp-2006-form-5.pdf

03750-kolnp-2006-international publication.pdf

03750-kolnp-2006-international search authority report.pdf

03750-kolnp-2006-others.pdf

03750-kolnp-2006-pct other document.pdf

03750-kolnp-2006-priority document.pdf

3750-KOLNP-2006-ABSTRACT.pdf

3750-KOLNP-2006-CANCELLED DOCOMENT.pdf

3750-KOLNP-2006-CLAIMS.pdf

3750-KOLNP-2006-CORRESPONDENCE-1.1.pdf

3750-KOLNP-2006-DESCRIPTION COMPLETE.pdf

3750-KOLNP-2006-FORM 1.pdf

3750-KOLNP-2006-FORM 2.pdf

3750-KOLNP-2006-FORM 26.pdf

3750-KOLNP-2006-FORM 3.pdf

3750-KOLNP-2006-FORM 5.pdf

3750-KOLNP-2006-FORM-27.pdf

3750-kolnp-2006-granted-abstract.pdf

3750-kolnp-2006-granted-claims.pdf

3750-kolnp-2006-granted-correspondence.pdf

3750-kolnp-2006-granted-description (complete).pdf

3750-kolnp-2006-granted-examination report.pdf

3750-kolnp-2006-granted-form 1.pdf

3750-kolnp-2006-granted-form 18.pdf

3750-kolnp-2006-granted-form 2.pdf

3750-kolnp-2006-granted-form 26.pdf

3750-kolnp-2006-granted-form 3.pdf

3750-kolnp-2006-granted-form 5.pdf

3750-kolnp-2006-granted-reply to examination report.pdf

3750-kolnp-2006-granted-specification.pdf

3750-kolnp-2006-granted-translated copy of priority document.pdf

3750-KOLNP-2006-OTHERS.pdf

3750-KOLNP-2006-PETITION UNDER RULE 137.pdf

3750-KOLNP-2006-REPLY TO EXAMINATION REPORT.pdf


Patent Number 236229
Indian Patent Application Number 3750/KOLNP/2006
PG Journal Number 42/2009
Publication Date 16-Oct-2009
Grant Date 12-Oct-2009
Date of Filing 13-Dec-2006
Name of Patentee SUMITOMO CHEMICAL COMPANY LIMITED
Applicant Address 27-1, SHINKAWA 2-CHOME, CHUO-KU, TOKYO
Inventors:
# Inventor's Name Inventor's Address
1 YOSHIHIDE NIIMOTO 42-2-17-701, KITAOOGI, HIGASHINADA-KU, KOBE-SHI, HYOGO
2 HIROHARU KUMAZAWA 42-2-607, AKAOJI-CHO, TAKATSUKI-SHI, OSAKA
3 OSAMU TOKUDA 2-4-3-204, GAKUENMIDORIGAOKA, NARA
4 FUMIAKI IBUKURO 9-19-406, MATSUYAMA-CHO, NISHINOMIYA-SHI, HYOGO
PCT International Classification Number C07C 231/12
PCT International Application Number PCT/JP2005/012011
PCT International Filing date 2005-06-23
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2004-186982 2004-06-24 Japan