SE459093B - 4-kloro-furo-(3,4-c)-pyridinderivat,foerfarande foe r framstaellning daerav och terapeutiska kompositioner innehaallande dem - Google Patents
4-kloro-furo-(3,4-c)-pyridinderivat,foerfarande foe r framstaellning daerav och terapeutiska kompositioner innehaallande demInfo
- Publication number
- SE459093B SE459093B SE8405118A SE8405118A SE459093B SE 459093 B SE459093 B SE 459093B SE 8405118 A SE8405118 A SE 8405118A SE 8405118 A SE8405118 A SE 8405118A SE 459093 B SE459093 B SE 459093B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- carbon atoms
- groups
- alkoxy
- dihydro
- Prior art date
Links
- 235000013305 food Nutrition 0.000 title description 2
- 239000000203 mixture Substances 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- REIGINRVLDUJCQ-UHFFFAOYSA-N 4-chlorofuro[3,4-c]pyridine Chemical class ClC1=NC=CC2=COC=C12 REIGINRVLDUJCQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- GFEZPGADIMGWOH-UHFFFAOYSA-N 6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical class CC1=NC=C2COCC2=C1O GFEZPGADIMGWOH-UHFFFAOYSA-N 0.000 claims description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 2
- 150000001721 carbon Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 238000002386 leaching Methods 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical class N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- KRFFDJKRFIRFEH-UHFFFAOYSA-N 3,3,6-trimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound CC1=NC=C2C(C)(C)OCC2=C1O KRFFDJKRFIRFEH-UHFFFAOYSA-N 0.000 description 1
- -1 3,4,5-trimethoxyphenyl-ethyl Chemical group 0.000 description 1
- WPRNMWVODLENAP-UHFFFAOYSA-N 3,6-dimethyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(C)OC2 WPRNMWVODLENAP-UHFFFAOYSA-N 0.000 description 1
- VFROHEFJKCMRAI-UHFFFAOYSA-N 3,6-dimethyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=CC=C1 VFROHEFJKCMRAI-UHFFFAOYSA-N 0.000 description 1
- JJGRSVSRPHZQGZ-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C=1C(=C(Cl)C=CC=1)Cl)C1=CC=CC=C1 JJGRSVSRPHZQGZ-UHFFFAOYSA-N 0.000 description 1
- LQEMUWNIWKVWOP-UHFFFAOYSA-N 3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=C(Cl)C=C1 LQEMUWNIWKVWOP-UHFFFAOYSA-N 0.000 description 1
- UHEZOMQCEAKBIE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=CC(OC)=CC=C1C1C(C=NC(C)=C2O)=C2CO1 UHEZOMQCEAKBIE-UHFFFAOYSA-N 0.000 description 1
- CZOLAEVRQAMQJD-UHFFFAOYSA-N 4-chloro-3,6-dimethyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=NC(C)=C(O)C2=C1C(C)OC2 CZOLAEVRQAMQJD-UHFFFAOYSA-N 0.000 description 1
- BJJGWGOGOMEECW-UHFFFAOYSA-N 4-chloro-3-(2,3-dichlorophenyl)-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C=1C(=C(Cl)C=CC=1)Cl)C1=CC=CC=C1 BJJGWGOGOMEECW-UHFFFAOYSA-N 0.000 description 1
- WLOGUAVGUVGOJB-UHFFFAOYSA-N 4-chloro-3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C)C1=CC=C(Cl)C=C1 WLOGUAVGUVGOJB-UHFFFAOYSA-N 0.000 description 1
- VKMQBPGTPDIYGP-UHFFFAOYSA-N 4-chloro-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC(Cl)=C2C1C1=CC=C(Cl)C=C1 VKMQBPGTPDIYGP-UHFFFAOYSA-N 0.000 description 1
- YYSDEJFOFNQOAW-UHFFFAOYSA-N 4-chloro-3-(4-methoxyphenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound COC1=CC=C(C=C1)C1OCC2=C1C(=NC(=C2O)C)Cl YYSDEJFOFNQOAW-UHFFFAOYSA-N 0.000 description 1
- SCVKXHUUQDXCGX-UHFFFAOYSA-N 4-chloro-6-methyl-3,3-diphenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C=1C=CC=CC=1)C1=CC=CC=C1 SCVKXHUUQDXCGX-UHFFFAOYSA-N 0.000 description 1
- JFRALSHFDCJIIA-UHFFFAOYSA-N 4-chloro-6-methyl-3-(2-phenylethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC(Cl)=C2C1CCC1=CC=CC=C1 JFRALSHFDCJIIA-UHFFFAOYSA-N 0.000 description 1
- NTXPKYQSEOLHGU-UHFFFAOYSA-N 4-chloro-6-methyl-3-(4-methylphenyl)-3-pentyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C)N=C2Cl)O)=C2C1(CCCCC)C1=CC=C(C)C=C1 NTXPKYQSEOLHGU-UHFFFAOYSA-N 0.000 description 1
- QDULDNCDVLEMKZ-UHFFFAOYSA-N 4-chloro-6-methyl-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC(Cl)=C2C1C1=CC=CC=C1 QDULDNCDVLEMKZ-UHFFFAOYSA-N 0.000 description 1
- IZUQTLUIHJUBRX-UHFFFAOYSA-N 4-chloro-6-methyl-3-propyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=NC(C)=C(O)C2=C1C(CCC)OC2 IZUQTLUIHJUBRX-UHFFFAOYSA-N 0.000 description 1
- HBLJSMREXQKFNU-UHFFFAOYSA-N 6-methyl-3,3-diphenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C=1C=CC=CC=1)C1=CC=CC=C1 HBLJSMREXQKFNU-UHFFFAOYSA-N 0.000 description 1
- AXZNOBIHGUZGPG-UHFFFAOYSA-N 6-methyl-3-(2-phenylethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1CCC1=CC=CC=C1 AXZNOBIHGUZGPG-UHFFFAOYSA-N 0.000 description 1
- JYFOHPOYHZRXBO-UHFFFAOYSA-N 6-methyl-3-(4-methylphenyl)-3-pentyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C)N=C2)O)=C2C1(CCCCC)C1=CC=C(C)C=C1 JYFOHPOYHZRXBO-UHFFFAOYSA-N 0.000 description 1
- VABUPDWURAFFTL-UHFFFAOYSA-N 6-methyl-3-propyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCC)OC2 VABUPDWURAFFTL-UHFFFAOYSA-N 0.000 description 1
- ARIQBLIVTNQIKZ-UHFFFAOYSA-N C12=C(O)C(C)=NC=C2C(C=2C=CC(Cl)=CC=2)OC1C(C=1)=CC=CC=1OCCN1CCCC1 Chemical compound C12=C(O)C(C)=NC=C2C(C=2C=CC(Cl)=CC=2)OC1C(C=1)=CC=CC=1OCCN1CCCC1 ARIQBLIVTNQIKZ-UHFFFAOYSA-N 0.000 description 1
- CVKNDPRBJVBDSS-UHFFFAOYSA-N Cicletanine Chemical compound O1CC2=C(O)C(C)=NC=C2C1C1=CC=C(Cl)C=C1 CVKNDPRBJVBDSS-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838327817A GB8327817D0 (en) | 1983-10-18 | 1983-10-18 | 4-halo-furo-(3 4-c)-pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8405118D0 SE8405118D0 (sv) | 1984-10-12 |
| SE8405118L SE8405118L (sv) | 1985-04-19 |
| SE459093B true SE459093B (sv) | 1989-06-05 |
Family
ID=10550364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8405118A SE459093B (sv) | 1983-10-18 | 1984-10-12 | 4-kloro-furo-(3,4-c)-pyridinderivat,foerfarande foe r framstaellning daerav och terapeutiska kompositioner innehaallande dem |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4585776A (is") |
| JP (1) | JPS60104090A (is") |
| AT (1) | AT391699B (is") |
| BE (1) | BE900780A (is") |
| CA (1) | CA1257270A (is") |
| CH (1) | CH662118A5 (is") |
| DE (1) | DE3438244A1 (is") |
| DK (1) | DK158003C (is") |
| DZ (1) | DZ687A1 (is") |
| ES (1) | ES536814A0 (is") |
| FI (1) | FI80036C (is") |
| FR (2) | FR2553286B1 (is") |
| GB (2) | GB8327817D0 (is") |
| HK (1) | HK54787A (is") |
| IE (1) | IE58041B1 (is") |
| IT (1) | IT1176986B (is") |
| LU (1) | LU85583A1 (is") |
| MA (1) | MA20251A1 (is") |
| NL (1) | NL8403181A (is") |
| OA (1) | OA07840A (is") |
| PT (2) | PT79369B (is") |
| SE (1) | SE459093B (is") |
| SG (1) | SG25387G (is") |
| ZA (1) | ZA847961B (is") |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| US6865862B2 (en) * | 2000-11-20 | 2005-03-15 | C.G. Bretting Mfg. Co., Inc. | Log bander apparatus and method |
| GB0221494D0 (en) * | 2002-09-16 | 2002-10-23 | Generics Uk Ltd | Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5621578B2 (is") * | 1973-06-02 | 1981-05-20 | ||
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| IN156817B (is") * | 1981-02-10 | 1985-11-09 | Scras |
-
1983
- 1983-10-18 GB GB838327817A patent/GB8327817D0/en active Pending
-
1984
- 1984-10-09 BE BE0/213802A patent/BE900780A/fr not_active IP Right Cessation
- 1984-10-10 LU LU85583A patent/LU85583A1/fr unknown
- 1984-10-10 CH CH4863/84A patent/CH662118A5/fr not_active IP Right Cessation
- 1984-10-11 ZA ZA847961A patent/ZA847961B/xx unknown
- 1984-10-11 GB GB08425704A patent/GB2148292B/en not_active Expired
- 1984-10-12 SE SE8405118A patent/SE459093B/sv not_active IP Right Cessation
- 1984-10-13 DZ DZ847301A patent/DZ687A1/fr active
- 1984-10-15 MA MA20475A patent/MA20251A1/fr unknown
- 1984-10-15 FI FI844034A patent/FI80036C/fi not_active IP Right Cessation
- 1984-10-16 US US06/661,376 patent/US4585776A/en not_active Expired - Lifetime
- 1984-10-17 IE IE266384A patent/IE58041B1/en not_active IP Right Cessation
- 1984-10-17 ES ES536814A patent/ES536814A0/es active Granted
- 1984-10-17 IT IT23176/84A patent/IT1176986B/it active
- 1984-10-17 DK DK495984A patent/DK158003C/da not_active IP Right Cessation
- 1984-10-17 JP JP59216483A patent/JPS60104090A/ja active Granted
- 1984-10-17 PT PT79369A patent/PT79369B/pt not_active IP Right Cessation
- 1984-10-18 FR FR8415947A patent/FR2553286B1/fr not_active Expired
- 1984-10-18 AT AT0332984A patent/AT391699B/de not_active IP Right Cessation
- 1984-10-18 CA CA000465804A patent/CA1257270A/en not_active Expired
- 1984-10-18 NL NL8403181A patent/NL8403181A/nl not_active Application Discontinuation
- 1984-10-18 FR FR8415948A patent/FR2553417B1/fr not_active Expired
- 1984-10-18 DE DE19843438244 patent/DE3438244A1/de active Granted
- 1984-10-18 OA OA58417A patent/OA07840A/xx unknown
- 1984-11-16 PT PT79512A patent/PT79512B/pt not_active IP Right Cessation
-
1987
- 1987-03-12 SG SG253/87A patent/SG25387G/en unknown
- 1987-07-23 HK HK547/87A patent/HK54787A/xx not_active IP Right Cessation
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