IE43704B1 - Benzofuranone compounds - Google Patents
Benzofuranone compoundsInfo
- Publication number
- IE43704B1 IE43704B1 IE501/76A IE50176A IE43704B1 IE 43704 B1 IE43704 B1 IE 43704B1 IE 501/76 A IE501/76 A IE 501/76A IE 50176 A IE50176 A IE 50176A IE 43704 B1 IE43704 B1 IE 43704B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- carbon atoms
- alkyl
- formula
- hydrogen
- Prior art date
Links
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- -1 methyl thio, hydroxy Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- KFDLHDGFDLHFRW-UHFFFAOYSA-N [O-][N+](Br)=O Chemical compound [O-][N+](Br)=O KFDLHDGFDLHFRW-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This invention provides new compounds of formula I, I wherein R1 is alkyl of 1 to 10 carbon atoms, cyclo alkyl of 3 to 8 carbon atoms or phenyl, R2 is hydrogen, nitro, lower alkyl, methylR3 is halogen, nitro, lower alkyl, methyl thio, hydroxy, lower alkoxy, acyloxy or acylamino, with the proviso that when R3 is in the 5 position, and R1 and R3 are identical and signify a straight alkyl chain of 1 to 5 carbon atoms, R2 is lower alkyl, useful as anti-phlogistics.
Description
The present invention relates to benzofuranone compounds.
In accordance with the invention there are provided new compounds of formula I, wherein Rj is alkyl of 1 to 10 carbon atoms, cyeloalkyl of 3 to 8 carbon atoms or phenyl, Rg is hydrogen or alkyl of 1 to 4 carbon atoms, and Rg is halogen, nitro, alkyl of 1 to 4 carbon atoms, methylthio, hydroxy, alkoxy of 1 to 4 carbon atoms, acyloxy of 1 to 4 carbon atoms or acylamino of 1 to 4 carbon atoms, with the proviso that when Rg is in the 5 position and Rj to Rg are identical and signify a straight alkyl chain of 1 to 4 carbon atoms, Rg is alkyl of 1 to 4 carbon atoms, and with the further proviso that when Rj is CHg and Rg is hydrogen, Rg is other than et -CHg; and w,ien Ri is cyclohexyl and Rg is hydrogen, Rg is other than -chloro.
Further, in accordance with the invention a compound of formula I may be obtained by a process comprising lactonizing a compound of formula II, II - 1 43704 wherein Rp R^ and R^ ar·' as defined above.
A group of compounds sui< ably prepared by this process are compounds of formula X as defined above with the further proviso that when R^ is alkyl of 1 to 5 carbon atoms and R^ is halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, Rg is lower alky) of 1 to 4 carbon atoms.
When R^ is cycloalkyl, this radical preferably signifies cyclopentyl or cycloheptyl, especially, however, cyclohexyl. When R^ is alkyl, this preferably contains 3 to 6, especially 3 or 4 carbon atoms and is preferably branched and specially signifies isobutyl or isopropyl.
When R2 is alkyl, tli is preferably signifies methyl.
The substituent Rj preferably signifies halogen, i.e. chlorine, bromine or fluorine, and preferably signifies chlorine. When R-, is alkyl or alkoxy, this esoecially contains or 2 carbon atoms. When R3 is an acyloxy or acylamino radical, this especially, contains carbon atoms. preferably is in the 5 position.
The lactonization of compounds of formula II in accordance with the process of the invention is effected in accordance with conventional methods, as described in Example 1. - 2 43704 The compounds of formula II, used as starting materials, may be obtairied in accordance with known methods. These compounds may be obtained in the usual manner from the corresponding compounds of formula II wherein Rg and Rg are hydrogen, and wherein the hydroxy group in the ring structure may optionally be protected temporarily by an alkoxy group, and the free carboxyl group may be protected temporarily by an ester group.
Example 1, which does not fora part of the invention, is 10 included,as an analogy example to illustrate the preparation of Examples 2 to 16 which do fora part of the invention. All temperatures are indicated in degrees Centigrade and are uncorrected.
EXAMPLE l·: 5-chloro-G-cyclohexy1-2,3-dihydrobenzofurany2-one g of 3'-chloro-4'-cyclohexy1-6'-hydroxyphenylacetic acid are dissolved in toluene with heating, 50 mg of p-toluenesulphonic acid are added, and the mixture is boiled in a water separator for 3 hours. The oil obtained after evaporation is purified on a 100-fold (Trade Mark) quantity of silica gel i-lercl;/ The desired product is eluted with chloroform and recrystallized from methylene chloride/petroleum ether. The crystals have an M.P. of 100-102°.
The following compounds of formula I are produced in analogous manner, whereby Rg, Rg and Rg have the following significances: ExampleR1R2R3 Melting point 2 Ό H 5-Br 124 - 126 ° 3 Ό II 7-Br 108 - 109 0 4 Ό II S-KO2 132 - 133 0 5 -o CHg 5-C1 92 - 93 0 6 o dg 5-KO2 94 - 95 ° 7 -o H 5-C1 111 - 112 ° ExampleR1R2R3 Melting point 8 -Ό H 5-CH3 157 - 158 0 9 OCH3 5-C1 88 - 89 0 10 H 5-CHg 77 - 78 0 11 -oCH3. 5-OCH3 amorphous 12 -o H 5-CH-CONH 3 195 - 196 ° 13 o H 5-CH3S 104 - 105 0 14 CH, CH\3 / 3 XCII ch2 H 5-C1 28 - 29 6 15 -D H 5-0H amorphous 16 H 5-CH3COO amorphous The compounds of formula X exhibit pharmacological activity. In particular they exhibit oedema and inflammation inhibitory activity as indicated in standard tests, for example in the carrageen oedema test, in the Adjuvans arthritis test and the granuloma cyst test in the rat and in the UV erythema test in the guinea-pig.
In standard tests the compounds of formula I exhibit further effects, such as an anti-pyretic effect, an analgesic effect, or an inhibition of PG synthetase or of Collagen-induced blood platelet aggregation.
The compounds are therefore indicated for use as inhibitors of oedemas and inflammations. An indicated daily dose is from 60 to 300 mg, conveniently administered in divided doses 2 to 4 times a day in unit dosage form containing from about 15 to about 150 mg of the compound, or in sustained release form.
The Example 7 compound exhibits especially interesting activity.
The present invention also provides a pharmaceutical composition comprising a compound of formula I, in association with a pharmaceutical carrier or diluent. Such compositions may be in the form of, for example, a solution or a tablet.
Conveniently there are provided compounds of formula I, wherein R^ is alkyl of 1 to 5 carbon atoms, R^ is hydrogen, and R^ is halogen, lower alkyl or lower alkoxy in the form of a pharmaceutical composition.
The compound of Example 1, a process for the preparation thereof and compositions containing this compound are described and claimed in our Patent Specification No. 43705.
Claims (28)
1. A process for the production oi benzofuranone compounds of formula I R. R. '3 ‘2 R, wherein R^ is alkyi of 1 to 10 carbon atoms, cyeloalkyl of 3 to 8 carbon atoms or phenyl, Rg is hydrogen or alkyl of 1 to 4 carbon atoms, and R 3 is halogen, nitro, alkyl of 1 to 4 carbon atoms, methylthio, hydroxy, alkoxy of 1 to 4 carbon atoms, acyloxy of 1 to 4 carbon atoms or acylamino of 1 to 4 carbon atoms, with the proviso that when Rg is in the 5 position and R.| and Rg are identical and signify a straight alkyl chain of 1 to 4 carbon atoms, Rg is alkyl of 1 to 4 carbon atoms, and with the further proviso that when R^ is CHg and Rg is hydrogen, Rg is other than -CHg; and when R^ is cyclohexyl and Rg is hydrogen, Rg is other than 5-chloro, comprising lactonizing a compound of formula II, R. ‘J COOH II R. OH wherein Rp Rg and Rg are as defined above. - 7 43704
2. A process according to claim 1 for the obtention of a compound of formula I as defined in claim 1 with the further proviso that when Rj is alkyl of 1 to 5 carbon atoms and R^ is halogen, alkyl or alkoxy, R 2 is lower alkyl.
3. A process for the production of a compound of formula I as defined in claim 1 or 2 substantially as hereinbefore defined with reference to any one of Examples 2 to 16.
4. A compound of formula I whenever produced by a process of claim 1, 2 or 3.
5. A compound of formula I as defined in claim 1.
6. A compound of claim 5, with the further proviso stated in claim 2.
7. A compound of claim 5 or 6 vzherein R 2? when alky^ is methyl and Rg is other than methylthio.
8. A compound of claim 5, wherein R^ is alkyl, alkoxy, acyloxy or acylamino.
9. A compound of claim 5, wherein R^ is cyclohexyl, R 2 is hydrogen and is nitro, bromine or chlorine.
10. A compound of claim 5, wherein R^ is cyclohexyl or phenyl, R 2 is hydrogen or methyl and R 3 is chlorine, nitro or methyl.
11. A compound of claim 4, 5, 6 or 7, v/herein Rg is halogen.
12. The compound of claim 5, wherein R^, Rg and Rg respectively are , H and 5-Br.
13. The compound of claim 5, wherein R^, Rg and Rg respectively are , H and 7-Br.
14. The compound of claim 5, wherein R^ z Rg and Rg respectively are , H and 5-NOg.
15. The compound of claim 5, v/herein Rg, Rg and Rg respectively are ' clI g and 5-Cl.
16. ·. The compound of claim 5, wherein R , Rg and Rg respectively are , CHg and 5-NOg. 15 if. The compound of claim 5, wherein Rg, Rg and Rg respectively are , H and 5-Cl. ig. The compound of claim 5, wherein Rg, Rg and Rg respectively are , H and 5-CHg.
17. 19,- The compound of claim 5, wherein Rg, Rg and Rg respectively are , CHg and 5-Cl.
18. 20. The compound of claim 5, wherein P:, R and
19. 21. The compound of claim 5, wherein R , R 2 and R^ respectively are , CH^ and 5-OCH3.
20. 22. The compound of claim 5, wherein R , R? and R^ respectively are , H and 5-CH 3 CONH.
21. 23. The compound of claim 5, wherein R^, R^ and R^ respectively are -o , II and 5-CH 3 S.
22. 24. The compound of claim 5, wherein R^, R 2 and R 3 respectively are H and 5-Cl. I
23. 25. The compound of claim 5, wherein R^, R 2 and R 3 respectively are , H and 5-0H.
24. 26. The compound of claim 5, vzherein R^, R 2 and R 3 II and 5-CH 3 COO. spectivaly are ,
25. 27, A pharmaceutical composition comprising a compound of any one of claims 4 to 26 in association with a pharmaceutical carrier or diluent.
26. 28, A pharmaceutical composition according to claim 27 comprising a compound of claim 5, wherein R^ is alkyl of 1 to 5 carbon atoms, 1' 2 is hydrogen and R 3 is halogen, lower alkyl or lower alkoxy.
27. 29. A pharmaceutical composition of claim 28, wherein ^CH in formula I R is -CH--CH , R. is H and R, is 5-C1 •L *· \ ___ z 3
28. 30. A pharmaceutical composition of claim 27, 28, or 5 29 in unit dosage form containing from 15 to 150 mg of the compound of formula I as an active agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE2465/80A IE43705B1 (en) | 1975-03-12 | 1976-03-10 | Benzofuranone derivative |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312975A CH614707A5 (en) | 1975-03-12 | 1975-03-12 | Process for the preparation of novel dihydrobenzofuranone derivatives |
| CH967875 | 1975-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43704L IE43704L (en) | 1976-09-12 |
| IE43704B1 true IE43704B1 (en) | 1981-05-06 |
Family
ID=25692258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE501/76A IE43704B1 (en) | 1975-03-12 | 1976-03-10 | Benzofuranone compounds |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51113864A (en) |
| AT (1) | AT357516B (en) |
| AU (1) | AU508681B2 (en) |
| CA (1) | CA1086757A (en) |
| DD (1) | DD125210A5 (en) |
| DE (1) | DE2608697A1 (en) |
| DK (1) | DK137274B (en) |
| ES (1) | ES445922A1 (en) |
| FI (1) | FI760548A (en) |
| FR (1) | FR2303540A1 (en) |
| GB (1) | GB1546701A (en) |
| IE (1) | IE43704B1 (en) |
| IL (1) | IL49192A (en) |
| NL (1) | NL7602393A (en) |
| NO (1) | NO760745L (en) |
| NZ (1) | NZ180273A (en) |
| PT (1) | PT64886B (en) |
| SE (1) | SE7603053L (en) |
| YU (1) | YU63576A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514415A (en) * | 1981-10-28 | 1985-04-30 | Ciba Geigy Corporation | Benzofuran-2(3H)-ones used as anti-inflammatory agents |
| US4849428A (en) * | 1987-11-23 | 1989-07-18 | The Procter & Gamble Company | Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use |
-
1976
- 1976-03-03 DE DE19762608697 patent/DE2608697A1/en not_active Withdrawn
- 1976-03-03 FI FI760548A patent/FI760548A/fi not_active Application Discontinuation
- 1976-03-03 DK DK92176AA patent/DK137274B/en not_active Application Discontinuation
- 1976-03-04 NO NO760745A patent/NO760745L/no unknown
- 1976-03-05 SE SE7603053A patent/SE7603053L/en unknown
- 1976-03-08 NL NL7602393A patent/NL7602393A/en not_active Application Discontinuation
- 1976-03-09 GB GB9315/76A patent/GB1546701A/en not_active Expired
- 1976-03-10 DD DD191782A patent/DD125210A5/xx unknown
- 1976-03-10 FR FR7606829A patent/FR2303540A1/en active Granted
- 1976-03-10 AT AT173876A patent/AT357516B/en not_active IP Right Cessation
- 1976-03-10 IL IL49192A patent/IL49192A/en unknown
- 1976-03-10 NZ NZ180273A patent/NZ180273A/en unknown
- 1976-03-10 IE IE501/76A patent/IE43704B1/en unknown
- 1976-03-10 ES ES445922A patent/ES445922A1/en not_active Expired
- 1976-03-10 CA CA247,552A patent/CA1086757A/en not_active Expired
- 1976-03-10 PT PT64886A patent/PT64886B/en unknown
- 1976-03-11 JP JP51025655A patent/JPS51113864A/en active Pending
- 1976-03-11 YU YU00635/76A patent/YU63576A/en unknown
- 1976-03-12 AU AU11970/76A patent/AU508681B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PT64886A (en) | 1976-03-31 |
| FI760548A (en) | 1976-09-13 |
| YU63576A (en) | 1982-05-31 |
| DK92176A (en) | 1976-09-13 |
| ES445922A1 (en) | 1977-08-16 |
| ATA173876A (en) | 1979-12-15 |
| FR2303540B1 (en) | 1979-07-20 |
| NL7602393A (en) | 1976-09-14 |
| IL49192A (en) | 1981-01-30 |
| NZ180273A (en) | 1978-03-06 |
| NO760745L (en) | 1976-09-14 |
| DE2608697A1 (en) | 1976-09-23 |
| AT357516B (en) | 1980-07-10 |
| DD125210A5 (en) | 1977-04-06 |
| SE7603053L (en) | 1976-09-13 |
| IL49192A0 (en) | 1976-05-31 |
| FR2303540A1 (en) | 1976-10-08 |
| CA1086757A (en) | 1980-09-30 |
| PT64886B (en) | 1977-11-17 |
| AU508681B2 (en) | 1980-03-27 |
| GB1546701A (en) | 1979-05-31 |
| IE43704L (en) | 1976-09-12 |
| JPS51113864A (en) | 1976-10-07 |
| DK137274B (en) | 1978-02-13 |
| AU1197076A (en) | 1977-09-15 |
| DK137274C (en) | 1978-07-17 |
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