PL123379B1 - Process for manufacturing novel esters - Google Patents
Process for manufacturing novel esters Download PDFInfo
- Publication number
- PL123379B1 PL123379B1 PL1980221888A PL22188880A PL123379B1 PL 123379 B1 PL123379 B1 PL 123379B1 PL 1980221888 A PL1980221888 A PL 1980221888A PL 22188880 A PL22188880 A PL 22188880A PL 123379 B1 PL123379 B1 PL 123379B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- water
- mmol
- value
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 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 24
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011664 nicotinic acid Substances 0.000 description 12
- 235000012000 cholesterol Nutrition 0.000 description 11
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 11
- 235000001968 nicotinic acid Nutrition 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 10
- 229960003512 nicotinic acid Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- -1 2-(p-chlorophenoxy) ethyl Chemical group 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 229960001214 clofibrate Drugs 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- GKUHMJCSBVHYAY-UHFFFAOYSA-N (2-benzoyl-4-chlorophenyl) pyridine-3-carboxylate Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1OC(=O)C1=CC=CN=C1 GKUHMJCSBVHYAY-UHFFFAOYSA-N 0.000 description 1
- KDWWTXCFEYTIEL-UHFFFAOYSA-N (2-cyclohexylphenyl) pyridine-3-carboxylate;hydron;chloride Chemical compound Cl.C=1C=CN=CC=1C(=O)OC1=CC=CC=C1C1CCCCC1 KDWWTXCFEYTIEL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-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
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 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
- VVMQAIJCWNJCMK-UHFFFAOYSA-N 2-chloro-4-cyclohexylphenol Chemical compound C1=C(Cl)C(O)=CC=C1C1CCCCC1 VVMQAIJCWNJCMK-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
- PJNMKAQCMGXVNI-UHFFFAOYSA-N 2-tert-butyl-4-cyclohexylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2CCCCC2)=C1 PJNMKAQCMGXVNI-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
- YUQPJMAOUVWWOM-UHFFFAOYSA-N 4-cyclohexyl-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1CCCCC1 YUQPJMAOUVWWOM-UHFFFAOYSA-N 0.000 description 1
- 208000031104 Arterial Occlusive disease Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- KFEOTLRYKZITRK-UHFFFAOYSA-N C1CCC(CC1)C2=CC(=C(C=C2)OC(=O)C3=CN=CC=C3)[N+](=O)[O-] Chemical compound C1CCC(CC1)C2=CC(=C(C=C2)OC(=O)C3=CN=CC=C3)[N+](=O)[O-] KFEOTLRYKZITRK-UHFFFAOYSA-N 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000015779 HDL Lipoproteins Human genes 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- BYYZKXCRMHXWIR-UHFFFAOYSA-N O=C(C1=CN=CC=C1)OC(C=CC(C1CCCCC1)=C1)=C1Cl Chemical compound O=C(C1=CN=CC=C1)OC(C=CC(C1CCCCC1)=C1)=C1Cl BYYZKXCRMHXWIR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 102000005583 Pyrin Human genes 0.000 description 1
- 108010059278 Pyrin Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- DBKLIGHGFZVBFK-UHFFFAOYSA-N [4-(1-adamantyl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(C23CC4CC(CC(C4)C2)C3)C=CC=1OC(=O)C1=CC=CN=C1 DBKLIGHGFZVBFK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HBKRFGSYVQCWSJ-UHFFFAOYSA-N [4-(2-phenylpropan-2-yl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(OC(=O)C=2C=NC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 HBKRFGSYVQCWSJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 208000021328 arterial occlusion Diseases 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000037396 body weight 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
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 229950008441 clofibric acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000008693 nausea Effects 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 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)
- Animal Behavior & Ethology (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)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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 |
|---|---|
| PL221888A1 PL221888A1 (US07943777-20110517-C00090.png) | 1980-10-20 |
| PL123379B1 true PL123379B1 (en) | 1982-10-30 |
Family
ID=6062456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980221888A PL123379B1 (en) | 1979-02-08 | 1980-02-08 | Process for manufacturing novel esters |
Country Status (22)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3891219T1 (de) * | 1988-01-22 | 1990-02-01 | Kh Nii Endokrinologii I Chimii | P-chlorphenoxysobuttersaeureundezylester und arzneimittel auf dessen grundlage zur behandlung der hyperlipidaemie |
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 IL IL59337A patent/IL59337A/xx not_active IP Right Cessation
- 1980-02-07 MX MX808635U patent/MX6377E/es unknown
- 1980-02-07 DK DK053680A patent/DK152360C/da not_active IP Right Cessation
- 1980-02-07 IE IE236/80A patent/IE49385B1/en not_active IP Right Cessation
- 1980-02-07 ES ES488345A patent/ES8101552A1/es not_active Expired
- 1980-02-08 IT IT19782/80A patent/IT1141197B/it active
- 1980-02-08 CA CA000345303A patent/CA1135689A/en not_active Expired
- 1980-02-08 BE BE0/199326A patent/BE881626A/fr not_active IP Right Cessation
- 1980-02-08 JP JP1374980A patent/JPS55129245A/ja active Granted
- 1980-02-08 AR AR279916A patent/AR228251A1/es active
- 1980-02-08 CH CH106380A patent/CH644092A5/de active IP Right Maintenance
- 1980-02-08 HU HU80289A patent/HU182099B/hu not_active IP Right Cessation
- 1980-02-08 NL NL8000826A patent/NL8000826A/nl not_active Application Discontinuation
- 1980-02-08 YU YU00338/80A patent/YU33880A/xx unknown
- 1980-02-08 GB GB8004310A patent/GB2041937B/en not_active Expired
- 1980-02-08 AU AU55355/80A patent/AU532208B2/en not_active Ceased
- 1980-02-08 FR FR8002783A patent/FR2448532A1/fr active Granted
- 1980-02-08 GR GR61163A patent/GR73905B/el unknown
- 1980-02-08 AT AT0070380A patent/AT374797B/de not_active IP Right Cessation
- 1980-02-08 PL PL1980221888A patent/PL123379B1/pl unknown
-
1985
- 1985-06-27 SG SG511/85A patent/SG51185G/en unknown
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