IE50546B1 - Derivatives of 1-aminopropan-2-ol - Google Patents
Derivatives of 1-aminopropan-2-olInfo
- Publication number
- IE50546B1 IE50546B1 IE2535/80A IE253580A IE50546B1 IE 50546 B1 IE50546 B1 IE 50546B1 IE 2535/80 A IE2535/80 A IE 2535/80A IE 253580 A IE253580 A IE 253580A IE 50546 B1 IE50546 B1 IE 50546B1
- Authority
- IE
- Ireland
- Prior art keywords
- thiophene
- tetrahydrobenzo
- carbon atoms
- imino
- radicals
- Prior art date
Links
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 alkyl radicals Chemical class 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- 229930192474 thiophene Natural products 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- KTHDRSYKYMKNEY-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzothiophene Chemical compound C1=CCCC2=C1SCC2 KTHDRSYKYMKNEY-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- CBKDCOKSXCTDAA-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzothiophene Chemical compound C1CCCC2=C1C=CS2 CBKDCOKSXCTDAA-UHFFFAOYSA-N 0.000 claims 2
- HTLTVBBCRXFMOQ-HAVVHWLPSA-N 1-(1-adamantyl)-1-amino-3-[(e)-6,7-dihydro-5h-1-benzothiophen-4-ylideneamino]oxypropan-2-ol Chemical compound C1C(C2)CC(C3)CC2CC13C(N)C(O)CO\N=C/1C(C=CS2)=C2CCC\1 HTLTVBBCRXFMOQ-HAVVHWLPSA-N 0.000 claims 1
- BDHLJZUDAXSEMZ-UHFFFAOYSA-N 1-(cyclododecylamino)-3-[(5-imino-6,7-dihydro-4H-1-benzothiophen-4-yl)oxy]propan-2-ol Chemical compound C1=2C=CSC=2CCC(=N)C1OCC(O)CNC1CCCCCCCCCCC1 BDHLJZUDAXSEMZ-UHFFFAOYSA-N 0.000 claims 1
- GZKMSCGAZNYRAM-BMRADRMJSA-N 1-[(e)-6,7-dihydro-5h-1-benzothiophen-4-ylideneamino]oxy-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C1CN(C)CCN1CC(O)CO\N=C/1C(C=CS2)=C2CCC\1 GZKMSCGAZNYRAM-BMRADRMJSA-N 0.000 claims 1
- KELIOZMTDOSCMM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene Chemical compound C1C=CC=C2SCCC21 KELIOZMTDOSCMM-UHFFFAOYSA-N 0.000 claims 1
- ZMNFPDADUSDNMW-UHFFFAOYSA-N C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1C(=N)CCC2=C1C=CS2 Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1C(=N)CCC2=C1C=CS2 ZMNFPDADUSDNMW-UHFFFAOYSA-N 0.000 claims 1
- MPOWZQDGGDZPCI-UHFFFAOYSA-N CC(C)NCC(COC1C(=N)CCC2=C1C=CS2)O Chemical compound CC(C)NCC(COC1C(=N)CCC2=C1C=CS2)O MPOWZQDGGDZPCI-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- QDKSUYMUAALPPJ-UHFFFAOYSA-N S1C=CC2=C1CC(=N)C2OCC(O)CNC(C)C Chemical compound S1C=CC2=C1CC(=N)C2OCC(O)CNC(C)C QDKSUYMUAALPPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 abstract 1
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- 208000019622 heart disease Diseases 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 22
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 14
- CQBVRNCDVAPGSH-BENRWUELSA-N (z)-n-(oxiran-2-ylmethoxy)-6,7-dihydro-5h-1-benzothiophen-4-imine Chemical compound C/1CCC=2SC=CC=2C\1=N/OCC1CO1 CQBVRNCDVAPGSH-BENRWUELSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000008602 contraction Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
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- 241000282472 Canis lupus familiaris Species 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- 231100000053 low toxicity Toxicity 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
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- VCZCAUSAQKWESF-ACCUITESSA-N (e)-n-(oxiran-2-ylmethoxy)-5,6,7,8-tetrahydrocyclohepta[b]thiophen-4-imine Chemical compound C\1CCCC=2SC=CC=2C/1=N/OCC1CO1 VCZCAUSAQKWESF-ACCUITESSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7931402A FR2471980A1 (fr) | 1979-12-21 | 1979-12-21 | Nouveaux derives de l'amino-1 propanol-2, leur procede de preparation et leur application therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE802535L IE802535L (en) | 1981-06-21 |
| IE50546B1 true IE50546B1 (en) | 1986-05-14 |
Family
ID=9233060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2535/80A IE50546B1 (en) | 1979-12-21 | 1980-12-04 | Derivatives of 1-aminopropan-2-ol |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4339450A (OSRAM) |
| EP (1) | EP0031266B1 (OSRAM) |
| JP (1) | JPS5699472A (OSRAM) |
| AR (1) | AR225937A1 (OSRAM) |
| AU (1) | AU541684B2 (OSRAM) |
| BE (1) | BE886471A (OSRAM) |
| BG (1) | BG35047A3 (OSRAM) |
| CA (1) | CA1158643A (OSRAM) |
| CH (1) | CH646165A5 (OSRAM) |
| CS (1) | CS228143B2 (OSRAM) |
| DE (1) | DE3061928D1 (OSRAM) |
| DK (1) | DK536180A (OSRAM) |
| ES (1) | ES497563A0 (OSRAM) |
| FR (1) | FR2471980A1 (OSRAM) |
| GB (1) | GB2066808B (OSRAM) |
| GR (1) | GR72831B (OSRAM) |
| HU (1) | HU181774B (OSRAM) |
| IE (1) | IE50546B1 (OSRAM) |
| IL (1) | IL61602A (OSRAM) |
| IN (1) | IN150867B (OSRAM) |
| IT (1) | IT1141642B (OSRAM) |
| LU (1) | LU83021A1 (OSRAM) |
| NZ (1) | NZ195786A (OSRAM) |
| PL (1) | PL127009B1 (OSRAM) |
| PT (1) | PT72247B (OSRAM) |
| RO (1) | RO80266B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704604A1 (de) * | 1987-02-13 | 1988-08-25 | Mack Chem Pharm | Oximether von 2,6-dioxabicyclo(3.3.0)octanonen, herstellungsverfahren und anwendung als arzneimittel |
| US4803286A (en) * | 1987-08-19 | 1989-02-07 | Merck & Co., Inc. | Amino-2-hydroxypropyloximinoheterocycle α-blockers |
| EP0347378A1 (de) * | 1988-06-13 | 1989-12-20 | Ciba-Geigy Ag | Imidazol-Derivate |
| IL103106A (en) | 1991-09-25 | 1998-06-15 | Sanofi Elf | Ethers of thienocyclopentanone oximes, their preparation and pharmaceutical compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3398161A (en) * | 1965-06-30 | 1968-08-20 | Ici Ltd | Benzo (b) thiophen derivatives which have beta-adrenergic blocking activity |
| NL6810133A (OSRAM) * | 1968-07-18 | 1970-01-20 |
-
1979
- 1979-12-21 FR FR7931402A patent/FR2471980A1/fr active Granted
-
1980
- 1980-11-15 GR GR63372A patent/GR72831B/el unknown
- 1980-11-18 GB GB8036920A patent/GB2066808B/en not_active Expired
- 1980-12-01 IL IL8061602A patent/IL61602A/xx unknown
- 1980-12-01 DE DE8080401713T patent/DE3061928D1/de not_active Expired
- 1980-12-01 EP EP80401713A patent/EP0031266B1/fr not_active Expired
- 1980-12-02 CH CH893680A patent/CH646165A5/fr not_active IP Right Cessation
- 1980-12-03 BE BE0/203024A patent/BE886471A/fr not_active IP Right Cessation
- 1980-12-04 IE IE2535/80A patent/IE50546B1/en unknown
- 1980-12-09 NZ NZ195786A patent/NZ195786A/xx unknown
- 1980-12-10 ES ES497563A patent/ES497563A0/es active Granted
- 1980-12-12 BG BG049969A patent/BG35047A3/xx unknown
- 1980-12-16 RO RO102863A patent/RO80266B/ro unknown
- 1980-12-17 AR AR283678A patent/AR225937A1/es active
- 1980-12-17 DK DK536180A patent/DK536180A/da not_active Application Discontinuation
- 1980-12-18 IT IT68942/80A patent/IT1141642B/it active
- 1980-12-18 CA CA000367082A patent/CA1158643A/en not_active Expired
- 1980-12-19 HU HU803060A patent/HU181774B/hu unknown
- 1980-12-19 PL PL1980228606A patent/PL127009B1/pl unknown
- 1980-12-19 LU LU83021A patent/LU83021A1/fr unknown
- 1980-12-19 CS CS809065A patent/CS228143B2/cs unknown
- 1980-12-19 AU AU65587/80A patent/AU541684B2/en not_active Ceased
- 1980-12-19 PT PT72247A patent/PT72247B/pt unknown
- 1980-12-22 US US06/219,213 patent/US4339450A/en not_active Expired - Fee Related
- 1980-12-22 JP JP18180280A patent/JPS5699472A/ja active Pending
-
1981
- 1981-01-17 IN IN54/CAL/81A patent/IN150867B/en unknown
Also Published As
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