JPS6135985B2 - - Google Patents
Info
- Publication number
- JPS6135985B2 JPS6135985B2 JP52005395A JP539577A JPS6135985B2 JP S6135985 B2 JPS6135985 B2 JP S6135985B2 JP 52005395 A JP52005395 A JP 52005395A JP 539577 A JP539577 A JP 539577A JP S6135985 B2 JPS6135985 B2 JP S6135985B2
- Authority
- JP
- Japan
- Prior art keywords
- quinoxaline
- formula
- carbon atoms
- represented
- following formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 244000144977 poultry Species 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 244000144972 livestock Species 0.000 claims description 6
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 claims description 5
- 241000588724 Escherichia coli Species 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 244000000010 microbial pathogen Species 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 208000018569 Respiratory Tract disease Diseases 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims 3
- 239000007952 growth promoter Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 241000282849 Ruminantia Species 0.000 description 5
- 241000282887 Suidae Species 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- IEEFRSBGHYKNOM-UHFFFAOYSA-N n-(2-cyanoethyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCCC#N IEEFRSBGHYKNOM-UHFFFAOYSA-N 0.000 description 2
- KAHLAAFLYJDGFP-UHFFFAOYSA-N n-(cyanomethyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCC#N KAHLAAFLYJDGFP-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YKAWOJYVXDCFDP-UHFFFAOYSA-N 3-cyanopropanamide Chemical compound NC(=O)CCC#N YKAWOJYVXDCFDP-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- TURHTASYUMWZCC-UHFFFAOYSA-N Olaquindox [BAN:INN] Chemical compound C1=CC=C2N([O-])C(C)=C(C(=O)NCCO)[N+](=O)C2=C1 TURHTASYUMWZCC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 210000004712 air sac Anatomy 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000427 carbadox Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BPMVRAQIQQEBLN-OBPBNMOMSA-N methyl n-[(e)-(1-hydroxy-4-oxidoquinoxalin-4-ium-2-ylidene)methyl]iminocarbamate Chemical compound C1=CC=C2N(O)C(=C/N=NC(=O)OC)/C=[N+]([O-])C2=C1 BPMVRAQIQQEBLN-OBPBNMOMSA-N 0.000 description 1
- ALHUXMDEZNLFTA-UHFFFAOYSA-N methyl-quinoxaline Natural products C1=CC=CC2=NC(C)=CN=C21 ALHUXMDEZNLFTA-UHFFFAOYSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229950010210 olaquindox Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002229 urogenital system Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH63476A CH627174A5 (en) | 1976-01-20 | 1976-01-20 | Process for the preparation of quinoxaline di-N-oxide derivatives |
| CH1492076 | 1976-11-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5289683A JPS5289683A (en) | 1977-07-27 |
| JPS6135985B2 true JPS6135985B2 (en18) | 1986-08-15 |
Family
ID=25685198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP539577A Granted JPS5289683A (en) | 1976-01-20 | 1977-01-20 | Quinoxalineediinnoxide derivative * its production and antiimicrobial composition containing same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4092415A (en18) |
| JP (1) | JPS5289683A (en18) |
| AU (1) | AU515192B2 (en18) |
| BR (1) | BR7700355A (en18) |
| CA (1) | CA1108143A (en18) |
| DE (1) | DE2701707C2 (en18) |
| DK (1) | DK141509B (en18) |
| EG (1) | EG13191A (en18) |
| ES (1) | ES455158A1 (en18) |
| FR (1) | FR2338935A1 (en18) |
| GB (1) | GB1569034A (en18) |
| HK (1) | HK41283A (en18) |
| IL (1) | IL51292A (en18) |
| KE (1) | KE3289A (en18) |
| MY (1) | MY8400251A (en18) |
| NL (1) | NL7700581A (en18) |
| NZ (1) | NZ183118A (en18) |
| SE (1) | SE427928B (en18) |
| SG (1) | SG28883G (en18) |
| SU (1) | SU890961A3 (en18) |
| YU (2) | YU39221B (en18) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT7869686A0 (it) * | 1978-11-24 | 1978-11-24 | Loranze Torino A | Procedimento di preparazione di 2metil 3 bidrossietilcarbamollchinossalina i.4 di n ossido puroed altri composti ad esso simili |
| US4418063A (en) * | 1978-12-19 | 1983-11-29 | Ciba-Geigy Corporation | Growth promoting quinoxaline-di-N-oxide carboxamides |
| US4254120A (en) * | 1978-12-19 | 1981-03-03 | Ciba-Geigy Corporation | Growth promoting quinoxaline-di-N-oxide carboxamides |
| DE3133888A1 (de) * | 1981-08-27 | 1983-03-10 | Bayer Ag | Wirkstoffkombination aus kitasamycin und chinoxalin-di-n-oxiden |
| JPH06701B2 (ja) * | 1983-12-01 | 1994-01-05 | 旭化成工業株式会社 | 動物用組成物 |
| BR112013015569B1 (pt) * | 2010-12-20 | 2020-03-03 | Dsm Ip Assets B.V. | Uso de moléculas orgânicas de nitrooxi na alimentação para reduzir a emissão de metano em ruminantes e/ou para melhorar o desempenho de ruminantes, composição nutricional ou aditivo nutricional de ruminantes |
| EP2644038A1 (en) * | 2012-03-26 | 2013-10-02 | DSM IP Assets B.V. | Use of para nitro amino derivatives in feed for reducing meth-ane emission in ruminants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670935C3 (de) * | 1967-10-04 | 1975-12-04 | Bayer Ag, 5090 Leverkusen | 2-Methyl-3-carbonsäureamidochinoxalin-1,4-dl-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel |
| GB1223720A (en) | 1968-10-30 | 1971-03-03 | Ici Ltd | Growth promotion |
| US3635972A (en) * | 1969-07-22 | 1972-01-18 | Pfizer | 3-methyl-2-quinoxalinecarboxamidedi-n-oxides |
-
1977
- 1977-01-10 SU SU772437355A patent/SU890961A3/ru active
- 1977-01-13 US US05/758,973 patent/US4092415A/en not_active Expired - Lifetime
- 1977-01-17 DE DE2701707A patent/DE2701707C2/de not_active Expired
- 1977-01-17 EG EG33/77A patent/EG13191A/xx active
- 1977-01-18 CA CA269,894A patent/CA1108143A/en not_active Expired
- 1977-01-19 BR BR7700355A patent/BR7700355A/pt unknown
- 1977-01-19 AU AU21443/77A patent/AU515192B2/en not_active Ceased
- 1977-01-19 DK DK20277AA patent/DK141509B/da not_active IP Right Cessation
- 1977-01-19 SE SE7700529A patent/SE427928B/xx not_active IP Right Cessation
- 1977-01-19 FR FR7701398A patent/FR2338935A1/fr active Granted
- 1977-01-19 IL IL51292A patent/IL51292A/xx unknown
- 1977-01-19 YU YU00135/77A patent/YU39221B/xx unknown
- 1977-01-19 ES ES455158A patent/ES455158A1/es not_active Expired
- 1977-01-19 NZ NZ183118A patent/NZ183118A/xx unknown
- 1977-01-20 NL NL7700581A patent/NL7700581A/xx not_active Application Discontinuation
- 1977-01-20 GB GB2356/77A patent/GB1569034A/en not_active Expired
- 1977-01-20 JP JP539577A patent/JPS5289683A/ja active Granted
-
1982
- 1982-07-13 YU YU1534/82A patent/YU40081B/xx unknown
-
1983
- 1983-05-20 KE KE3289A patent/KE3289A/xx unknown
- 1983-05-24 SG SG288/83A patent/SG28883G/en unknown
- 1983-10-13 HK HK412/83A patent/HK41283A/xx unknown
-
1984
- 1984-12-30 MY MY251/84A patent/MY8400251A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2144377A (en) | 1978-07-27 |
| NZ183118A (en) | 1979-12-11 |
| YU153482A (en) | 1982-10-31 |
| YU39221B (en) | 1984-08-31 |
| SE7700529L (sv) | 1977-07-21 |
| AU515192B2 (en) | 1981-03-19 |
| GB1569034A (en) | 1980-06-11 |
| YU40081B (en) | 1985-06-30 |
| NL7700581A (nl) | 1977-07-22 |
| FR2338935B1 (en18) | 1979-03-23 |
| DK141509B (da) | 1980-04-08 |
| HK41283A (en) | 1983-10-21 |
| MY8400251A (en) | 1984-12-31 |
| DK20277A (en18) | 1977-07-21 |
| CA1108143A (en) | 1981-09-01 |
| SU890961A3 (ru) | 1981-12-15 |
| DE2701707A1 (de) | 1977-07-21 |
| SE427928B (sv) | 1983-05-24 |
| DE2701707C2 (de) | 1986-05-22 |
| FR2338935A1 (fr) | 1977-08-19 |
| EG13191A (en) | 1980-12-31 |
| JPS5289683A (en) | 1977-07-27 |
| SG28883G (en) | 1984-04-19 |
| US4092415A (en) | 1978-05-30 |
| BR7700355A (pt) | 1977-09-20 |
| IL51292A0 (en) | 1977-03-31 |
| ES455158A1 (es) | 1978-04-01 |
| YU13577A (en) | 1982-10-31 |
| IL51292A (en) | 1981-06-29 |
| DK141509C (en18) | 1980-09-29 |
| KE3289A (en) | 1983-06-17 |
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