SE450381B - Estrar av nikotinsyra och 2-(p-klorfenoxi)-isosmorsyra till anvendning som lipidsenkande medel - Google Patents
Estrar av nikotinsyra och 2-(p-klorfenoxi)-isosmorsyra till anvendning som lipidsenkande medelInfo
- Publication number
- SE450381B SE450381B SE8000962A SE8000962A SE450381B SE 450381 B SE450381 B SE 450381B SE 8000962 A SE8000962 A SE 8000962A SE 8000962 A SE8000962 A SE 8000962A SE 450381 B SE450381 B SE 450381B
- Authority
- SE
- Sweden
- Prior art keywords
- nicotinate
- acid addition
- acid
- addition salt
- pharmaceutically usable
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 13
- 150000002632 lipids Chemical class 0.000 title description 5
- 239000003795 chemical substances by application Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
- 235000001968 nicotinic acid Nutrition 0.000 claims description 6
- 239000011664 nicotinic acid Substances 0.000 claims description 6
- -1 p-chlorophenoxy Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- QCGOZOLLKOPOTM-UHFFFAOYSA-N (2-cyclohexylphenyl) pyridine-3-carboxylate Chemical group C=1C=CN=CC=1C(=O)OC1=CC=CC=C1C1CCCCC1 QCGOZOLLKOPOTM-UHFFFAOYSA-N 0.000 claims description 3
- KDWWTXCFEYTIEL-UHFFFAOYSA-N (2-cyclohexylphenyl) pyridine-3-carboxylate;hydron;chloride Chemical group Cl.C=1C=CN=CC=1C(=O)OC1=CC=CC=C1C1CCCCC1 KDWWTXCFEYTIEL-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- YUJPABSYWMRDOH-UHFFFAOYSA-N (4-cyclododecylphenyl) pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C=C1)=CC=C1C1CCCCCCCCCCC1 YUJPABSYWMRDOH-UHFFFAOYSA-N 0.000 claims description 2
- GMOLIFGBTIYCGT-UHFFFAOYSA-N 4-[2-(1-adamantyl)phenyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1C1=CC=CC=C1C1(C2)CC(C3)CC2CC3C1 GMOLIFGBTIYCGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- UHMDBYRPFFWVIH-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-yl pyridine-3-carboxylate Chemical compound C=1C=CC=2CCCCC=2C=1OC(=O)C1=CC=CN=C1 UHMDBYRPFFWVIH-UHFFFAOYSA-N 0.000 claims description 2
- DQFQTZGYPLXEDG-UHFFFAOYSA-N [4-(2-cyclohexylacetyl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(OC(=O)C=2C=NC=CC=2)C=CC=1C(=O)CC1CCCCC1 DQFQTZGYPLXEDG-UHFFFAOYSA-N 0.000 claims description 2
- CUZYGTJIGATQSB-UHFFFAOYSA-N [4-[2-(1-adamantyl)acetyl]phenyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(C(=O)CC23CC4CC(CC(C4)C2)C3)C=CC=1OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 CUZYGTJIGATQSB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003524 antilipemic agent Substances 0.000 claims description 2
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 5
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960003512 nicotinic acid Drugs 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- WZPVEPWPLQMODU-UHFFFAOYSA-N (4-cyclohexylphenyl) pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C=C1)=CC=C1C1CCCCC1 WZPVEPWPLQMODU-UHFFFAOYSA-N 0.000 description 1
- HTXIBSPLKGAJRX-UHFFFAOYSA-N 2-(1-adamantyl)-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1(C2)CC(C3)CC2CC3C1 HTXIBSPLKGAJRX-UHFFFAOYSA-N 0.000 description 1
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 description 1
- OZUQBIVVKGATPZ-UHFFFAOYSA-N 2-cyclohexyl-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1CCCCC1 OZUQBIVVKGATPZ-UHFFFAOYSA-N 0.000 description 1
- KZMYFIUFUAOZHP-UHFFFAOYSA-N 4-(1-adamantyl)phenol Chemical compound C1=CC(O)=CC=C1C1(C2)CC(C3)CC2CC3C1 KZMYFIUFUAOZHP-UHFFFAOYSA-N 0.000 description 1
- JNAUIOQFUDVUJP-UHFFFAOYSA-N 4-cyclododecylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCCCCCCCC1 JNAUIOQFUDVUJP-UHFFFAOYSA-N 0.000 description 1
- SCWNNOCLLOHZIG-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1-naphthol Chemical compound C1CCCC2=C1C=CC=C2O SCWNNOCLLOHZIG-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- ZGUWJIPHRXAEDM-UHFFFAOYSA-N CN(CCC1)C1C(C=C1)=CN=C1C(C=C1)=CC=C1C(CC1CCCCC1)=O Chemical compound CN(CCC1)C1C(C=C1)=CN=C1C(C=C1)=CC=C1C(CC1CCCCC1)=O ZGUWJIPHRXAEDM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- IBTWUVRCFHJPKN-UHFFFAOYSA-N hydron;pyridine-3-carboxylic acid;chloride Chemical compound Cl.OC(=O)C1=CC=CN=C1 IBTWUVRCFHJPKN-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2904757 | 1979-02-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8000962L SE8000962L (sv) | 1980-08-09 |
| SE450381B true SE450381B (sv) | 1987-06-22 |
Family
ID=6062456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8000962A SE450381B (sv) | 1979-02-08 | 1980-02-06 | Estrar av nikotinsyra och 2-(p-klorfenoxi)-isosmorsyra till anvendning som lipidsenkande medel |
Country Status (22)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02502998A (ja) * | 1988-01-22 | 1990-09-20 | ハルコフスキ ナウチノ‐イススレドバテルスキ インスティテュト エンドクリノロギイ イ ヒミイ ゴルモノフ | ｎ‐クロロフェノキシイソ酪酸ウンデシルエステルおよびそれを基剤とした高類脂血症の治療用医薬製剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3175M (fr) * | 1963-06-25 | 1965-03-08 | Analyses Et De Rech S Biolog M | Nouveaux composés chimiques a action vaso-dilatatrice périphérique. |
| DE2352012A1 (de) * | 1972-11-01 | 1974-05-09 | Ciba Geigy Ag | Neue aliphatisch substituierte arylchalkogeno-kohlenwasserstoffderivate und verfahren zu ihrer herstellung |
| ES438246A1 (es) * | 1975-06-04 | 1977-01-16 | Alter Sa | Un procedimiento de preparacion del glicol 2-(p-clorofenoci)-2-metilpropinato nicotinato. |
| JPS57102866A (en) * | 1980-12-19 | 1982-06-26 | Kyorin Pharmaceut Co Ltd | Nicotinic acid derivative and its preparation |
-
1980
- 1980-02-06 SE SE8000962A patent/SE450381B/sv not_active IP Right Cessation
- 1980-02-07 ES ES488345A patent/ES8101552A1/es not_active Expired
- 1980-02-07 IL IL59337A patent/IL59337A/xx not_active IP Right Cessation
- 1980-02-07 MX MX808635U patent/MX6377E/es unknown
- 1980-02-07 IE IE236/80A patent/IE49385B1/en not_active IP Right Cessation
- 1980-02-07 DK DK053680A patent/DK152360C/da not_active IP Right Cessation
- 1980-02-08 HU HU80289A patent/HU182099B/hu not_active IP Right Cessation
- 1980-02-08 IT IT19782/80A patent/IT1141197B/it active
- 1980-02-08 PL PL1980221888A patent/PL123379B1/pl unknown
- 1980-02-08 AU AU55355/80A patent/AU532208B2/en not_active Ceased
- 1980-02-08 GB GB8004310A patent/GB2041937B/en not_active Expired
- 1980-02-08 BE BE0/199326A patent/BE881626A/fr not_active IP Right Cessation
- 1980-02-08 CH CH106380A patent/CH644092A5/de not_active IP Right Cessation
- 1980-02-08 JP JP1374980A patent/JPS55129245A/ja active Granted
- 1980-02-08 CA CA000345303A patent/CA1135689A/en not_active Expired
- 1980-02-08 YU YU00338/80A patent/YU33880A/xx unknown
- 1980-02-08 GR GR61163A patent/GR73905B/el unknown
- 1980-02-08 AR AR279916A patent/AR228251A1/es active
- 1980-02-08 FR FR8002783A patent/FR2448532A1/fr active Granted
- 1980-02-08 AT AT0070380A patent/AT374797B/de not_active IP Right Cessation
- 1980-02-08 NL NL8000826A patent/NL8000826A/nl not_active Application Discontinuation
-
1985
- 1985-06-27 SG SG511/85A patent/SG51185G/en unknown
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