DK142622B - Analogifremgangsmåde til fremstilling af indolizinderivater eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af indolizinderivater eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK142622B DK142622B DK72677AA DK72677A DK142622B DK 142622 B DK142622 B DK 142622B DK 72677A A DK72677A A DK 72677AA DK 72677 A DK72677 A DK 72677A DK 142622 B DK142622 B DK 142622B
- Authority
- DK
- Denmark
- Prior art keywords
- indolizine
- benzoyl
- hydrogen
- phenyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 56
- 230000008569 process Effects 0.000 title claims description 23
- 150000003839 salts Chemical class 0.000 title claims description 19
- 239000002253 acid Substances 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title 1
- -1 dibromophenyl group Chemical group 0.000 claims description 145
- 150000001875 compounds Chemical class 0.000 claims description 108
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 85
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 23
- 150000002478 indolizines Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CFNARKJATWTEDG-UHFFFAOYSA-N OC(=O)C(O)=O.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(C=2C=CC(Cl)=CC=2)C=C2N1C=CC=C2 Chemical compound OC(=O)C(O)=O.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(C=2C=CC(Cl)=CC=2)C=C2N1C=CC=C2 CFNARKJATWTEDG-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 229940126062 Compound A Drugs 0.000 description 35
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 35
- 239000000047 product Substances 0.000 description 31
- 229960004592 isopropanol Drugs 0.000 description 28
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 27
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- 238000012360 testing method Methods 0.000 description 25
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- 241000282472 Canis lupus familiaris Species 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 238000001990 intravenous administration Methods 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 15
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- 206010002383 Angina Pectoris Diseases 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 210000004165 myocardium Anatomy 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- 230000003288 anthiarrhythmic effect Effects 0.000 description 11
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical class C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 11
- 230000033764 rhythmic process Effects 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 239000003416 antiarrhythmic agent Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 229940090044 injection Drugs 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 230000000144 pharmacologic effect Effects 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ROCHZUNCIZLTRQ-UHFFFAOYSA-N oxalic acid;propan-2-ol Chemical compound CC(C)O.OC(=O)C(O)=O ROCHZUNCIZLTRQ-UHFFFAOYSA-N 0.000 description 9
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 8
- 230000002763 arrhythmic effect Effects 0.000 description 8
- BUBNOQUZOCSBNU-UHFFFAOYSA-N benzene oxalic acid Chemical compound C1=CC=CC=C1.C(C(=O)O)(=O)O BUBNOQUZOCSBNU-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229960002748 norepinephrine Drugs 0.000 description 8
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- DZCKBBOUTRRMKD-UHFFFAOYSA-N CO.C=1C=CN2C=CC=CC12 Chemical compound CO.C=1C=CN2C=CC=CC12 DZCKBBOUTRRMKD-UHFFFAOYSA-N 0.000 description 7
- 206010003119 arrhythmia Diseases 0.000 description 7
- 238000010253 intravenous injection Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
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- 230000036284 oxygen consumption Effects 0.000 description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 5
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- 230000001515 vagal effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB668076 | 1976-02-19 | ||
| GB6680/76A GB1518443A (en) | 1976-02-19 | 1976-02-19 | Indolizine derivatives and process for preparing the same |
| GB3331476 | 1976-08-10 | ||
| GB3331476 | 1976-08-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK72677A DK72677A (en, 2012) | 1977-08-20 |
| DK142622B true DK142622B (da) | 1980-12-01 |
| DK142622C DK142622C (en, 2012) | 1981-08-03 |
Family
ID=26240878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK72677AA DK142622B (da) | 1976-02-19 | 1977-02-18 | Analogifremgangsmåde til fremstilling af indolizinderivater eller syreadditionssalte deraf. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4103012A (en, 2012) |
| JP (1) | JPS52125193A (en, 2012) |
| AR (2) | AR211887A1 (en, 2012) |
| AT (1) | AT358035B (en, 2012) |
| AU (1) | AU505894B2 (en, 2012) |
| CA (1) | CA1071198A (en, 2012) |
| CH (2) | CH617697A5 (en, 2012) |
| DE (1) | DE2707048C2 (en, 2012) |
| DK (1) | DK142622B (en, 2012) |
| ES (2) | ES456039A1 (en, 2012) |
| FI (1) | FI61030C (en, 2012) |
| FR (1) | FR2341578A1 (en, 2012) |
| GR (1) | GR59328B (en, 2012) |
| IE (1) | IE44941B1 (en, 2012) |
| IT (1) | IT1085862B (en, 2012) |
| NL (1) | NL164283C (en, 2012) |
| NO (1) | NO145842C (en, 2012) |
| NZ (1) | NZ183377A (en, 2012) |
| OA (1) | OA05575A (en, 2012) |
| PT (1) | PT66199B (en, 2012) |
| SE (1) | SE420314B (en, 2012) |
| YU (3) | YU39489B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ193926A (en) * | 1979-07-06 | 1984-05-31 | Labaz Sanofi Nv | 2-(alkyl or phenyl)-3(4-hydroxybenzoyl)indolizines |
| US4378362A (en) * | 1979-12-06 | 1983-03-29 | S.A. Labaz N.V. | Indolizine derivatives and process for preparing the same |
| FR2495616A1 (fr) * | 1980-12-09 | 1982-06-11 | Labaz Nv | Nouveaux derives d'indolizine, leur procede de preparation ainsi que leurs applications en therapeutique |
| US4520026A (en) * | 1981-02-06 | 1985-05-28 | S. A. Labaz N.V. | Indolizine derivatives and use as cardiovascular agents |
| FR2528845A1 (fr) * | 1982-06-17 | 1983-12-23 | Sanofi Sa | Nouveaux derives d'indolizine, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
| JPS59113802U (ja) * | 1983-01-14 | 1984-08-01 | オムロン株式会社 | 制御装置 |
| US5215988A (en) * | 1986-02-14 | 1993-06-01 | Sanofi | Aminoalkoxyphenyl derivatives, process of preparation and compositions containing the same |
| FR2594438B1 (fr) * | 1986-02-14 | 1990-01-26 | Labaz Sanofi Nv | Derives d'indolizine, leur procede de preparation ainsi que les compositions en contenant |
| NZ221717A (en) * | 1986-09-10 | 1990-08-28 | Sandoz Ltd | Azaindole and indolizine derivatives and pharmaceutical compositions |
| IL87181A (en) * | 1987-08-07 | 1993-08-18 | Sanofi Sa | Aminoalkoxyphenyl derivatives, their preparation and pharmaceutical and veterinary compositions containing them |
| US4880824A (en) * | 1987-09-21 | 1989-11-14 | Ortho Pharmaceutical Corporation | Phenyl and benzoyl substituted imidazo-fused heterocyclic calcium channel blockers |
| FR2642755B1 (en, 2012) * | 1989-02-07 | 1993-11-05 | Sanofi | |
| FR2642756B1 (fr) * | 1989-02-07 | 1994-03-04 | Sanofi | Derives cycloaminoalkoxyphenyle, leur procede de preparation ainsi que les compositions pharmaceutiques ou veterinaires en contenant |
| FR2665444B1 (fr) * | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
| FR2893616B1 (fr) * | 2005-11-23 | 2008-01-04 | Sanofi Aventis Sa | Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant |
| FR2967412B1 (fr) | 2010-11-17 | 2012-12-14 | Sanofi Aventis | Nouveaux derives d'indolizine, leur preparation et leur application en therapeutique |
| CN110283167A (zh) * | 2018-11-14 | 2019-09-27 | 贵州省中国科学院天然产物化学重点实验室 | 一种抗心率失常药物布托普洛嗪的制备方法 |
-
1977
- 1977-01-31 FI FI770318A patent/FI61030C/fi not_active IP Right Cessation
- 1977-02-02 GR GR52693A patent/GR59328B/el unknown
- 1977-02-11 AT AT92077A patent/AT358035B/de not_active IP Right Cessation
- 1977-02-14 CH CH180877A patent/CH617697A5/fr not_active IP Right Cessation
- 1977-02-15 FR FR7704171A patent/FR2341578A1/fr active Granted
- 1977-02-16 PT PT66199A patent/PT66199B/pt unknown
- 1977-02-16 US US05/769,332 patent/US4103012A/en not_active Expired - Lifetime
- 1977-02-17 AU AU22394/77A patent/AU505894B2/en not_active Expired
- 1977-02-17 SE SE7701771A patent/SE420314B/xx not_active IP Right Cessation
- 1977-02-17 NL NL7701678.A patent/NL164283C/xx not_active IP Right Cessation
- 1977-02-17 YU YU428/77A patent/YU39489B/xx unknown
- 1977-02-18 NO NO770547A patent/NO145842C/no unknown
- 1977-02-18 CA CA272,103A patent/CA1071198A/en not_active Expired
- 1977-02-18 DK DK72677AA patent/DK142622B/da not_active IP Right Cessation
- 1977-02-18 ES ES456039A patent/ES456039A1/es not_active Expired
- 1977-02-18 IE IE361/77A patent/IE44941B1/en unknown
- 1977-02-18 IT IT20434/77A patent/IT1085862B/it active
- 1977-02-18 NZ NZ183377A patent/NZ183377A/xx unknown
- 1977-02-18 AR AR266608A patent/AR211887A1/es active
- 1977-02-18 DE DE2707048A patent/DE2707048C2/de not_active Expired
- 1977-02-18 JP JP1768977A patent/JPS52125193A/ja active Granted
- 1977-02-19 OA OA56077A patent/OA05575A/xx unknown
- 1977-11-30 AR AR270182A patent/AR212791A1/es active
-
1978
- 1978-03-01 ES ES467441A patent/ES467441A1/es not_active Expired
-
1979
- 1979-11-30 CH CH1068079A patent/CH623322A5/fr not_active IP Right Cessation
-
1982
- 1982-08-23 YU YU1890/82A patent/YU42791B/xx unknown
-
1983
- 1983-11-16 YU YU2251/83A patent/YU42888B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |