CA1050544A - Process for the preparation of 2-acylamino-benzylamines - Google Patents
Process for the preparation of 2-acylamino-benzylaminesInfo
- Publication number
- CA1050544A CA1050544A CA205,415A CA205415A CA1050544A CA 1050544 A CA1050544 A CA 1050544A CA 205415 A CA205415 A CA 205415A CA 1050544 A CA1050544 A CA 1050544A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- prepared
- reacting
- chloro
- benzylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
This invention relates to a new process for the preparation of 2-acylamino - benzylamines having valuable pharmacological properties and/or being intermediates for the preparations of valuable pharmacologically active compounds. The new process comprises the reaction of the corresponding benzoxazines with appropriate primary or secondary amino compounds. Examples of the preparation of certain 2-acylamino - benzylamines by means of the new process are given. The benzoxazines compounds used as starting materials are also new and a process for thier preparation is described and exemplified.
This invention relates to a new process for the preparation of 2-acylamino - benzylamines having valuable pharmacological properties and/or being intermediates for the preparations of valuable pharmacologically active compounds. The new process comprises the reaction of the corresponding benzoxazines with appropriate primary or secondary amino compounds. Examples of the preparation of certain 2-acylamino - benzylamines by means of the new process are given. The benzoxazines compounds used as starting materials are also new and a process for thier preparation is described and exemplified.
Description
59~
This invention relates to a new process for the preparation of 2-acylamino - benzylamine derivatives having valuable pharmacological activity and/or being intermediates for the preparation of valuable pharmacologically active compounds.
The preparation of 2-amino-benzylamines by reacting the corresponding 4H-3, 1-benzoxazines with amines is known from the literature (see for example R. C.
Elderfield "Heterocyclic Compour.ds"~ Vol. 6, page 574).
According to the present invention there is provided a process for the preparation of' compounds of general formula .
~ R3 ,: ~H R~
1 Rl , (wherein Hal represents a chlorine or bromine atom, Rl .. : .
"' '' ~
" ' , , - 2 -, , ' ' .
5~
represents a hydrogen or bromine atom; R2 represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R3 represents a cyclohexyl, hydroxycyclohexyl, isopropylaminocarbonylmethyl or morpholinocarbonylmethyl group, and R4 represents a benzoyl group) and pharmaceu~ically acceptable acid addition salts thereof which comprises reacting a compound of formula Hal ~ ~ CH2\ (II) R~ ~C-R4' Cwherein Hal and Rl are as hereinbefore defined and R4' represents a phenyl group) with a compound of formula H N (III) Cwherein R2 and R3 are as hereinbefore defined) and if desired subsequently converting the compound of formula I thus obtained into a pharmaceutically acceptable acid addition salt thereof, ~ :
The present invention also relates to compounds of general ~-formula I as previously defined and pharmaceutically acceptable acid addition salts thereof whenever prepared by a process as described above.
.'",',:' . .. ...
.. ... .
, ~. . .
~L~5(3 5~ :
The group R4' is the compound of formula II may for example represent a phenyl, 2-chlorophenyl or 4-methyl :~
phenyl groupO ~
Using the process according to the invention we .
have prepared compounds of general formula I and acid addition salts thereof in excellent yields.
The reaction is conveniently carr1ed out in the :-presence of a solvent, for example tetraline, or in the : presence of an excess of~the amine of formula III used, at temperatures from 100 to 200 C, preferably, however, at temperatures from 130 to 180 C. The reaction may, however, also be carried out in the absence of a solvent.
The compounds of general formula I thereby obtained may~ if desired, be subsequently converted into --: their acid addition salts, preferably their physiologically ~ .
,' ~' ''. ' , . ' .
. .
., : i:
., . .: : . , '.
~. . . .
~L~5054~ ~
compatib.le acid addition salts, with inorganic or organic acids. Suitable acids for this purpose include for example hydrochloric acid, hydrobromic acid, sulfuric acid) .
phosphoric acid, lactic acid, citric acid and maleic acid. ~ . ;.-The coinpounds of general for.~ul~
Hal,~ R 7 Rl \ N~ 4 (II ) (wherein Hal. represents a chlorine or bromine atom, R
represellts a hydrogen, chlorine or bromine atom and ~4' represents an aryl group, for example a pheny].~ 2-chlorophenyl or 4;methyl.phenyl ~roup).and acid ~ddition ~salts thereof are new compounds and constitute a furtller ; .
f~ature of the present invention. They may be prepared . .
, ~ according to the following process:
', Dehydration of a compound of ~ormula Ua}~cH2--OH (IV) ', , ' ' ~ ,.
: - 5 -,. .
, ' , .
. .. ., , . .. , ......................... , . , .,,,, . .. :, .. ... . . .. ... . . .. .
~,, . ,., ." .,. -,; ,,., , . . , ., .. : , ,,. .,, .. , , .. , . , ., .. ~,; ,.".. ,, :. . . . .
~ L~5~544 (wherein ~lal and Rl are as hereinbeforedefined ~nd R4 represents an aromatic organic acyl group).
The dehydration is conveniently effected by mea~s of a dehydrating agent, advantageouc].y a mineral acid, for example hydrochloric acid, hydrobromic acid, sulph~ric acid or phosphoric acid `
The reaction is preferably carried out in the presen-ce of a solvent,for example ether, tetrahydrofuran or dio~ane conveniently at temperatures frorn.0 to 50C, preferablyj however, at temperatures frorn 15 to 25C.
- The benzyl of general formula IV used as starting materials may.for example be obtained by reaction of the corresponding ~ -amino~benzyl alcohols (which rnay be obtained by reduction of the corresponding benzaldehydes with ~sodium borohydride) with appropriate aromatic acid halides ln pyridlne and subsequent alkaline saponifica-tion of the esters formed.
s .s 6 ~ :
,; i :
~~, ,, ' ' i ~
, , ': ' . . , ' . '. ': :
, , , , , , , : ~ ,, .:.
:
~5054~
The following Examples serve to illustrate the preparation of compounds of general formula I and II
as h~reln dcfined, and acid addition salts thereof, I :
in accordance with the present invention: <
Examl~l.e A
.
6~Di.~ro~o - 2-~heny]-4H-3~ l-~enzoxaæine .. ..
600 ml of absolute ether were added to 11 g of 2 benzoylamino-3,5-dibromo benzyl alcohol. Gaseous `~
hydrogen bromide was introduced into the mixture for ~: 30 minutes whilst stirring. 6,8-Dibromo-2-phenyl- ~ .
: . 3,1-beDzoxazine hydrobromide precipitated out of the : starting solution. After stirring for 6 hours, the precipitate was suction filtered and recrystalized from .. ...
absolute ethanol ~M.p. of the~hydrobromide: 218 to 221C. `
:~ 5-Chioro-2-phenyl-4H-3,1-benzoxazine M.p.: 88.5 to 89. 5C
.
I - 7 ~ ~
, .
'', . ~"''':`'. ' ', . , ~ .:'. '-.
, , ~, . .
. ' ' . ~
':
~LED5~
Prepared from 2-benzoylamino-6-chloro-benzyl alcohol analogously to Example A.
Example 1
This invention relates to a new process for the preparation of 2-acylamino - benzylamine derivatives having valuable pharmacological activity and/or being intermediates for the preparation of valuable pharmacologically active compounds.
The preparation of 2-amino-benzylamines by reacting the corresponding 4H-3, 1-benzoxazines with amines is known from the literature (see for example R. C.
Elderfield "Heterocyclic Compour.ds"~ Vol. 6, page 574).
According to the present invention there is provided a process for the preparation of' compounds of general formula .
~ R3 ,: ~H R~
1 Rl , (wherein Hal represents a chlorine or bromine atom, Rl .. : .
"' '' ~
" ' , , - 2 -, , ' ' .
5~
represents a hydrogen or bromine atom; R2 represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R3 represents a cyclohexyl, hydroxycyclohexyl, isopropylaminocarbonylmethyl or morpholinocarbonylmethyl group, and R4 represents a benzoyl group) and pharmaceu~ically acceptable acid addition salts thereof which comprises reacting a compound of formula Hal ~ ~ CH2\ (II) R~ ~C-R4' Cwherein Hal and Rl are as hereinbefore defined and R4' represents a phenyl group) with a compound of formula H N (III) Cwherein R2 and R3 are as hereinbefore defined) and if desired subsequently converting the compound of formula I thus obtained into a pharmaceutically acceptable acid addition salt thereof, ~ :
The present invention also relates to compounds of general ~-formula I as previously defined and pharmaceutically acceptable acid addition salts thereof whenever prepared by a process as described above.
.'",',:' . .. ...
.. ... .
, ~. . .
~L~5(3 5~ :
The group R4' is the compound of formula II may for example represent a phenyl, 2-chlorophenyl or 4-methyl :~
phenyl groupO ~
Using the process according to the invention we .
have prepared compounds of general formula I and acid addition salts thereof in excellent yields.
The reaction is conveniently carr1ed out in the :-presence of a solvent, for example tetraline, or in the : presence of an excess of~the amine of formula III used, at temperatures from 100 to 200 C, preferably, however, at temperatures from 130 to 180 C. The reaction may, however, also be carried out in the absence of a solvent.
The compounds of general formula I thereby obtained may~ if desired, be subsequently converted into --: their acid addition salts, preferably their physiologically ~ .
,' ~' ''. ' , . ' .
. .
., : i:
., . .: : . , '.
~. . . .
~L~5054~ ~
compatib.le acid addition salts, with inorganic or organic acids. Suitable acids for this purpose include for example hydrochloric acid, hydrobromic acid, sulfuric acid) .
phosphoric acid, lactic acid, citric acid and maleic acid. ~ . ;.-The coinpounds of general for.~ul~
Hal,~ R 7 Rl \ N~ 4 (II ) (wherein Hal. represents a chlorine or bromine atom, R
represellts a hydrogen, chlorine or bromine atom and ~4' represents an aryl group, for example a pheny].~ 2-chlorophenyl or 4;methyl.phenyl ~roup).and acid ~ddition ~salts thereof are new compounds and constitute a furtller ; .
f~ature of the present invention. They may be prepared . .
, ~ according to the following process:
', Dehydration of a compound of ~ormula Ua}~cH2--OH (IV) ', , ' ' ~ ,.
: - 5 -,. .
, ' , .
. .. ., , . .. , ......................... , . , .,,,, . .. :, .. ... . . .. ... . . .. .
~,, . ,., ." .,. -,; ,,., , . . , ., .. : , ,,. .,, .. , , .. , . , ., .. ~,; ,.".. ,, :. . . . .
~ L~5~544 (wherein ~lal and Rl are as hereinbeforedefined ~nd R4 represents an aromatic organic acyl group).
The dehydration is conveniently effected by mea~s of a dehydrating agent, advantageouc].y a mineral acid, for example hydrochloric acid, hydrobromic acid, sulph~ric acid or phosphoric acid `
The reaction is preferably carried out in the presen-ce of a solvent,for example ether, tetrahydrofuran or dio~ane conveniently at temperatures frorn.0 to 50C, preferablyj however, at temperatures frorn 15 to 25C.
- The benzyl of general formula IV used as starting materials may.for example be obtained by reaction of the corresponding ~ -amino~benzyl alcohols (which rnay be obtained by reduction of the corresponding benzaldehydes with ~sodium borohydride) with appropriate aromatic acid halides ln pyridlne and subsequent alkaline saponifica-tion of the esters formed.
s .s 6 ~ :
,; i :
~~, ,, ' ' i ~
, , ': ' . . , ' . '. ': :
, , , , , , , : ~ ,, .:.
:
~5054~
The following Examples serve to illustrate the preparation of compounds of general formula I and II
as h~reln dcfined, and acid addition salts thereof, I :
in accordance with the present invention: <
Examl~l.e A
.
6~Di.~ro~o - 2-~heny]-4H-3~ l-~enzoxaæine .. ..
600 ml of absolute ether were added to 11 g of 2 benzoylamino-3,5-dibromo benzyl alcohol. Gaseous `~
hydrogen bromide was introduced into the mixture for ~: 30 minutes whilst stirring. 6,8-Dibromo-2-phenyl- ~ .
: . 3,1-beDzoxazine hydrobromide precipitated out of the : starting solution. After stirring for 6 hours, the precipitate was suction filtered and recrystalized from .. ...
absolute ethanol ~M.p. of the~hydrobromide: 218 to 221C. `
:~ 5-Chioro-2-phenyl-4H-3,1-benzoxazine M.p.: 88.5 to 89. 5C
.
I - 7 ~ ~
, .
'', . ~"''':`'. ' ', . , ~ .:'. '-.
, , ~, . .
. ' ' . ~
':
~LED5~
Prepared from 2-benzoylamino-6-chloro-benzyl alcohol analogously to Example A.
Example 1
2-Benzoylamino-N-cyclohex~1-3~5-dibromo-N-methyl-benzylamine 11.2 g (0.025 mol) of 6.8-dibromo-2-phenyl-4H-3,1-benzoxazine hydrobromide were refluxed with 17.0 g (0.15 mol) of N-methyl-cyclohexylamine for 1.5 hours. Subsequently, the reaction mixture was mixed with 2N sodium hydroxide solution and extracted several times with ether and the organic layer was then dried over sodium sulfate and evaporated to dryness. The residue was dissolved in absolute ethanol and ether and the solution was acidified with ethanolic hydrochloric acid, whereby the 2-benzoylamino-N-cyclohexyl-3,5-dibromo-N-methyl-benzylamine hydrochloride crystallized ou~.
Yield: 12.1 g (93.7~ of theory), m.p.: 270 to 272 C (decomp.).
Example 2 2=Benzoylamino-6-chloro-N-methyl-N-(morpholino-carbonyl-methyl)-benzylamine M.p.: 122.5 to 123 C.
Prepared from 5-chloro-2-phenyl-4H-3,1-benzoxazine and sarcosine morpholide analogously to Example 1.
Example 3 2-Benzoy_amino-6-chloro~N-isopropyl-N-(mor~holino=carbo~yl-methyl)-benzylamine M.p.: 125 to 127 C.
Prepared from 5-chloro-2-phenyl-4H-3,1-benzoxazine and N-isopropyl-glycine morpholide analogously to Example 1.
Example 4 2-Benzoy mino-4-chloro-N-methyl-N-(isopro~ylamino-c_rbonyl~methyl)-benzylamine -~
M.p.: 140 to 142 C.
Prepared from 7-chloro-2-phenyl 4H-3,1-benzoxazine and sarcosine isopropyl-amide analogously to Example 1.
..
-. , , , . . , .. .. :. , : , . :
: .. : . . . : :
, . , . :. , ., . .. . : . ...
~5~
Example 5 -Benzoylamino-6-bromo-N-(morpholino-carbonyl-meth~)benzylamine M.P.: 159 to 161 C.
Prepared from 5-bromo-2-phenyl-4H-3,1-benzoxazine and sarcosine morpholide analogously to Example 1.
Example 6 2-Benzoylamino-3,5-dibromo-N-methyl-N-(morpholino-carbonyl-methyl)-benzylamine M.p.: 164 to 166 C.
10 Prepared from 6,8 dibromo-2-phenyl-4H-3,1-benzoxazine and sarcosine morpho-lide analogouslyto Example 1.
_ g - '~.
.'.
Yield: 12.1 g (93.7~ of theory), m.p.: 270 to 272 C (decomp.).
Example 2 2=Benzoylamino-6-chloro-N-methyl-N-(morpholino-carbonyl-methyl)-benzylamine M.p.: 122.5 to 123 C.
Prepared from 5-chloro-2-phenyl-4H-3,1-benzoxazine and sarcosine morpholide analogously to Example 1.
Example 3 2-Benzoy_amino-6-chloro~N-isopropyl-N-(mor~holino=carbo~yl-methyl)-benzylamine M.p.: 125 to 127 C.
Prepared from 5-chloro-2-phenyl-4H-3,1-benzoxazine and N-isopropyl-glycine morpholide analogously to Example 1.
Example 4 2-Benzoy mino-4-chloro-N-methyl-N-(isopro~ylamino-c_rbonyl~methyl)-benzylamine -~
M.p.: 140 to 142 C.
Prepared from 7-chloro-2-phenyl 4H-3,1-benzoxazine and sarcosine isopropyl-amide analogously to Example 1.
..
-. , , , . . , .. .. :. , : , . :
: .. : . . . : :
, . , . :. , ., . .. . : . ...
~5~
Example 5 -Benzoylamino-6-bromo-N-(morpholino-carbonyl-meth~)benzylamine M.P.: 159 to 161 C.
Prepared from 5-bromo-2-phenyl-4H-3,1-benzoxazine and sarcosine morpholide analogously to Example 1.
Example 6 2-Benzoylamino-3,5-dibromo-N-methyl-N-(morpholino-carbonyl-methyl)-benzylamine M.p.: 164 to 166 C.
10 Prepared from 6,8 dibromo-2-phenyl-4H-3,1-benzoxazine and sarcosine morpho-lide analogouslyto Example 1.
_ g - '~.
.'.
Claims (13)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of compounds of general formula (I) (wherein Hal represents a chlorine or bromine atom; R1 represents a hydrogen or bromine atom, R2 represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R3 represents a cyclohexyl, hydroxycyclohexyl, isopropylaminocarbonylmethyl or morpholinocarbonylmethyl group; and R4 represents benzoyl group) and pharmaceutically acceptable acid addition salts thereof which comprises reacting a compound of formula (II) (wherein Hal and R1 are as hereinbefore defined and R4' represents a phenyl group) with a compound of formula (III) (wherein R2 and R3 are as hereinbefore defined) and if desired subsequently converting the compound of formula I thus obtained into a pharmaceutically acceptable acid addition salt thereof.
2. A process as claimed in claim 1 wherein the group R4' in the com-pound of formula II used is a phenyl, 2-chlorophenyl or 4-methylphenyl group.
3. A process as claimed in claim 1 or claim 2 wherein the reaction is effected in the presence of a solvent.
4. A process as claimed in claim 1 or claim 2 wherein the reaction is effected in the presence of an excess of the amine of formula III used.
5. A process as claimed in claim 1 or claim 2 wherein the reaction is effected at temperatures from 100 to 200°C.
6. Compounds of general formula 1 as defined in claim 1 and pharmaceutically acceptable acid addition salts thereof whenever prepared by a process as claimed in claim 1 or by an obvious equivalent thereof.
7. A process according to claim 1 in which 2-benzoyl-N-cyclohexyl-3,5-dibromo-N-methylbenzylamine and its hydrochloride is prepared by reacting 6,8-dibromo-2-phenyl-4H-3,1-benzoxazine hydrobromide with excess N-methyl-cyclohexylamine and when the hydrochloride is required reacting the base so obtained with hydrogen chloride.
8. A process according to claim 1 in which 2-benzoylamino-6-chloro-N-methyl-N-(morpholinocarbonylmethyl)benzylamine is prepared by reacting 5-chloro-2-phenyl-4H-3,1-benzoxazine with sarcosine morpholide.
9. A process according to claim 1 in which 2-benzoylamino-6-chloro-N-isopropyl-N-(morpholinocarbonylmethyl)benzylamine is prepared by reacting 5-chloro-2-phenyl-4H-3,1-benzoxazine with N-isopropylglycine morpholide.
10. A process according to claim 1 in which 2-benzoylamino-4-chloro-N-methyl-N-(isopropylaminocarbonylmethyl)benzylamine is prepared by reacting 7-chloro-2-phenyl-4H-3,1-benzoxazine with sarcosine isopropylamide.
11. A process according to claim 1 in which 2-benzoylamino-6-bromo-N-(morpholinocarbonylmethyl)benzylamine is prepared by reacting 5-bromo-2-phenyl-4H-3,1-benzoxazine with sarcosine morpholide.
12. A process according to claim 1 in which 2-benzoylamino-3,5-dibromo-N-methyl-N-(morpholinocarbonylmethyl)benzylamine is prepared by reacting 6,8-dibromo-2-phenyl-4H-3,1-benzoxazine with sarcosine morpholide.
13. 2-Benzoylamino-6-chloro-N-methyl-N-(morpholinocarbonylmethyl)-benzylamine whenever prepared by the process of claim 8 or by an obvious chemical equivalent thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337456 DE2337456A1 (en) | 1973-07-24 | 1973-07-24 | NEW PROCESS FOR THE PRODUCTION OF 2-ACYLAMINO-BENZYLAMINES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050544A true CA1050544A (en) | 1979-03-13 |
Family
ID=5887784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA205,415A Expired CA1050544A (en) | 1973-07-24 | 1974-07-23 | Process for the preparation of 2-acylamino-benzylamines |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5817456B2 (en) |
| AT (1) | AT333262B (en) |
| BG (1) | BG23744A3 (en) |
| CA (1) | CA1050544A (en) |
| CH (2) | CH605866A5 (en) |
| DK (1) | DK140009C (en) |
| ES (1) | ES427951A1 (en) |
| FI (1) | FI61311C (en) |
| HU (1) | HU167972B (en) |
| NL (1) | NL7409722A (en) |
| PL (1) | PL91391B1 (en) |
| SE (2) | SE413893B (en) |
| YU (1) | YU36366B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6378894B2 (en) * | 2014-02-27 | 2018-08-22 | 国立大学法人東京工業大学 | Trifluoromethyl group-containing oxazines and method for producing the same |
-
1974
- 1974-06-11 FI FI1775/74A patent/FI61311C/en active
- 1974-06-20 AT AT510774A patent/AT333262B/en not_active IP Right Cessation
- 1974-06-26 BG BG027081A patent/BG23744A3/en unknown
- 1974-07-01 YU YU01844/74A patent/YU36366B/en unknown
- 1974-07-04 ES ES0427951A patent/ES427951A1/en not_active Expired
- 1974-07-18 NL NL7409722A patent/NL7409722A/en not_active Application Discontinuation
- 1974-07-22 CH CH1453677A patent/CH605866A5/xx not_active IP Right Cessation
- 1974-07-22 CH CH1007774A patent/CH603562A5/en not_active IP Right Cessation
- 1974-07-22 HU HUTO970A patent/HU167972B/en unknown
- 1974-07-23 JP JP49084539A patent/JPS5817456B2/en not_active Expired
- 1974-07-23 DK DK396774A patent/DK140009C/en not_active IP Right Cessation
- 1974-07-23 SE SE7409585A patent/SE413893B/en unknown
- 1974-07-23 CA CA205,415A patent/CA1050544A/en not_active Expired
- 1974-07-23 PL PL1974172935A patent/PL91391B1/pl unknown
-
1977
- 1977-04-06 SE SE7704094A patent/SE7704094L/en unknown
-
1982
- 1982-11-15 JP JP57200254A patent/JPS6027672B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK396774A (en) | 1975-03-10 |
| FI61311B (en) | 1982-03-31 |
| DK140009B (en) | 1979-06-05 |
| CH603562A5 (en) | 1978-08-31 |
| JPS5041834A (en) | 1975-04-16 |
| HU167972B (en) | 1976-01-28 |
| YU184474A (en) | 1981-11-13 |
| JPS5817456B2 (en) | 1983-04-07 |
| YU36366B (en) | 1983-06-30 |
| BG23744A3 (en) | 1977-10-12 |
| DK140009C (en) | 1979-11-05 |
| JPS58154563A (en) | 1983-09-14 |
| ATA510774A (en) | 1976-03-15 |
| JPS6027672B2 (en) | 1985-06-29 |
| FI61311C (en) | 1982-07-12 |
| PL91391B1 (en) | 1977-02-28 |
| FI177574A (en) | 1975-01-25 |
| SE7409585L (en) | 1975-01-27 |
| SE7704094L (en) | 1977-04-06 |
| ES427951A1 (en) | 1976-09-01 |
| AT333262B (en) | 1976-11-10 |
| SE413893B (en) | 1980-06-30 |
| CH605866A5 (en) | 1978-10-13 |
| NL7409722A (en) | 1975-01-28 |
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