SE500670C2 - Pyrrolidin- och piperidonföreningar och farmaceutiska kompositioner innehållande dessa - Google Patents
Pyrrolidin- och piperidonföreningar och farmaceutiska kompositioner innehållande dessaInfo
- Publication number
- SE500670C2 SE500670C2 SE8902608A SE8902608A SE500670C2 SE 500670 C2 SE500670 C2 SE 500670C2 SE 8902608 A SE8902608 A SE 8902608A SE 8902608 A SE8902608 A SE 8902608A SE 500670 C2 SE500670 C2 SE 500670C2
- Authority
- SE
- Sweden
- Prior art keywords
- hydrogen
- group
- tert
- represent
- butyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 17
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 title abstract description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000004480 active ingredient Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- -1 3,5-Di-tert-butyl-4-hydroxyphenyl Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- OWJSEESROFTAQV-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)pyrrolidin-2-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(N2C(CCC2)=O)=C1 OWJSEESROFTAQV-UHFFFAOYSA-N 0.000 claims description 17
- 231100000252 nontoxic Toxicity 0.000 claims description 17
- 230000003000 nontoxic effect Effects 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003435 aroyl group Chemical group 0.000 claims description 14
- 125000001589 carboacyl group Chemical group 0.000 claims description 14
- BUTFGOBRFTXPDC-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)piperidin-2-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(N2C(CCCC2)=O)=C1 BUTFGOBRFTXPDC-UHFFFAOYSA-N 0.000 claims description 13
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 239000004615 ingredient Substances 0.000 claims description 12
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- LDEZZVQURRAGOR-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-3h-isoindol-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(N2C(C3=CC=CC=C3C2)=O)=C1 LDEZZVQURRAGOR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000000144 pharmacologic effect Effects 0.000 claims description 4
- XZNHGIZBPOKOJN-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-3-methylpyrrolidin-2-one Chemical group O=C1C(C)CCN1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XZNHGIZBPOKOJN-UHFFFAOYSA-N 0.000 claims description 3
- MUGYKCLRYKGKBB-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-4-methylpyrrolidin-2-one Chemical compound O=C1CC(C)CN1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 MUGYKCLRYKGKBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 13
- 239000003937 drug carrier Substances 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 31
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- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 3
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical class O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
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- 238000012360 testing method Methods 0.000 description 21
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- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- YTJXGDYAEOTOCG-UHFFFAOYSA-N lithium;di(propan-2-yl)azanide;oxolane Chemical compound [Li+].C1CCOC1.CC(C)[N-]C(C)C YTJXGDYAEOTOCG-UHFFFAOYSA-N 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- WOGVSFZYKQTBKV-UHFFFAOYSA-N methylsulfinylmethane;hydroiodide Chemical group [I-].C[SH+](C)=O WOGVSFZYKQTBKV-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
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- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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- 239000012730 sustained-release form Substances 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/248,942 US4959482A (en) | 1988-09-26 | 1988-09-26 | Pyrrolidinone compounds and pharamaceutical compositions containing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8902608D0 SE8902608D0 (sv) | 1989-07-27 |
| SE8902608L SE8902608L (sv) | 1990-03-27 |
| SE500670C2 true SE500670C2 (sv) | 1994-08-08 |
Family
ID=22941364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8902608A SE500670C2 (sv) | 1988-09-26 | 1989-07-27 | Pyrrolidin- och piperidonföreningar och farmaceutiska kompositioner innehållande dessa |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4959482A (fr) |
| JP (1) | JPH02129167A (fr) |
| AU (1) | AU3893289A (fr) |
| BE (1) | BE1003692A4 (fr) |
| DE (1) | DE3932068A1 (fr) |
| FR (1) | FR2636947B1 (fr) |
| GB (1) | GB2223014B (fr) |
| SE (1) | SE500670C2 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5128330A (en) * | 1991-02-19 | 1992-07-07 | Biofor, Ltd. | Oxazinone substituted phosphines |
| US5256091A (en) * | 1991-11-06 | 1993-10-26 | Outboard Marine Corporation | Shift interlock system |
| WO1993010117A1 (fr) * | 1991-11-15 | 1993-05-27 | American Cyanamid Company | Procede de preparation d'un agent de reticulation triazine tris-lactame, et compositions durcissables contenant cet agent |
| KR20090035695A (ko) * | 2006-08-09 | 2009-04-10 | 스미스클라인 비참 코포레이션 | 프로게스테론 수용체 조정인자로서의 피롤리디논 아닐린 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754141A (fr) * | 1969-08-04 | 1971-02-01 | Pfizer | Esters d'alpha-carboxyarylmethyl penicillines |
| US3717659A (en) * | 1970-06-09 | 1973-02-20 | Merck & Co Inc | Heterocyclic salicylic acid derivatives |
| US3718743A (en) * | 1970-11-19 | 1973-02-27 | Merck & Co Inc | 5-phenyl-2-piperidones and 5-phenyl-2-thiopiperidones in compositions and methods for treating pain, fever and inflammation |
| US3790597A (en) * | 1971-04-12 | 1974-02-05 | Ciba Geigy Corp | Sulfur derivatives of alkylhydroxyphenyl maleimides and compositions thereof |
| US3906002A (en) * | 1973-12-28 | 1975-09-16 | John F Stephen | Hindered phenolic norbornane-2,3-dicarboximides |
| US4172082A (en) * | 1977-05-16 | 1979-10-23 | Riker Laboratories, Inc. | Substituted thiophenes |
| US4124725A (en) * | 1977-05-16 | 1978-11-07 | Riker Laboratories, Inc. | Anti-inflammatory method |
| US4636516A (en) * | 1981-02-19 | 1987-01-13 | Yamanouchi Pharmaceutical Co., Ltd. | 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds |
| US4357345A (en) * | 1981-11-23 | 1982-11-02 | Riker Laboratories, Inc. | Substituted furans |
| JPS5965071A (ja) * | 1982-09-02 | 1984-04-13 | ザ・ウエルカム・フアウンデ−シヨン・リミテツド | 鎮痛、抗炎症剤 |
| US4743606A (en) * | 1986-03-25 | 1988-05-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | 3-[2-(3',5'-di-t-butyl-4'-hydroxyphenyl)ethenyl]pyridine having anti-inflammatory and anti-arthritic properties |
-
1988
- 1988-09-26 US US07/248,942 patent/US4959482A/en not_active Expired - Fee Related
-
1989
- 1989-07-25 AU AU38932/89A patent/AU3893289A/en not_active Abandoned
- 1989-07-27 SE SE8902608A patent/SE500670C2/sv unknown
- 1989-08-30 FR FR8911400A patent/FR2636947B1/fr not_active Expired - Fee Related
- 1989-09-05 BE BE8900947A patent/BE1003692A4/fr not_active IP Right Cessation
- 1989-09-07 GB GB8920270A patent/GB2223014B/en not_active Expired - Fee Related
- 1989-09-26 JP JP1248226A patent/JPH02129167A/ja active Pending
- 1989-09-26 DE DE3932068A patent/DE3932068A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US4959482A (en) | 1990-09-25 |
| SE8902608L (sv) | 1990-03-27 |
| AU3893289A (en) | 1990-03-29 |
| GB8920270D0 (en) | 1989-10-18 |
| FR2636947B1 (fr) | 1994-10-28 |
| GB2223014A (en) | 1990-03-28 |
| GB2223014B (en) | 1992-03-18 |
| JPH02129167A (ja) | 1990-05-17 |
| BE1003692A4 (fr) | 1992-05-26 |
| DE3932068A1 (de) | 1990-03-29 |
| SE8902608D0 (sv) | 1989-07-27 |
| FR2636947A1 (fr) | 1990-03-30 |
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