PL164662B1 - Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5]dekanu PL PL PL - Google Patents
Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5]dekanu PL PL PLInfo
- Publication number
- PL164662B1 PL164662B1 PL90291648A PL29164890A PL164662B1 PL 164662 B1 PL164662 B1 PL 164662B1 PL 90291648 A PL90291648 A PL 90291648A PL 29164890 A PL29164890 A PL 29164890A PL 164662 B1 PL164662 B1 PL 164662B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- decane
- alkyl
- oxa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 title description 16
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000000524 functional group Chemical group 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
- 239000012458 free base Substances 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- LQGLKWIXYWZNGB-UHFFFAOYSA-N 1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical class O1C(=O)NCC11CCNCC1 LQGLKWIXYWZNGB-UHFFFAOYSA-N 0.000 claims 1
- RAPAKELQTSIJRM-UHFFFAOYSA-N 1-[4,4-bis(4-fluorophenyl)but-3-enyl]-4-ethynylpiperidin-4-ol;hydrochloride Chemical compound Cl.C1CC(O)(C#C)CCN1CCC=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 RAPAKELQTSIJRM-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- WYDMNGYRWISCLZ-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)prop-2-enyl]-4-ethynylpiperidin-4-ol;hydrochloride Chemical compound Cl.C1CC(O)(C#C)CCN1CC=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 WYDMNGYRWISCLZ-UHFFFAOYSA-N 0.000 abstract 1
- VLVWUSGOTSWICZ-UHFFFAOYSA-N [1-[4,4-bis(4-fluorophenyl)but-3-enyl]-4-ethynylpiperidin-4-yl] n-benzylcarbamate Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=CCCN1CCC(C#C)(OC(=O)NCC=2C=CC=CC=2)CC1 VLVWUSGOTSWICZ-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 206010021143 Hypoxia Diseases 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 210000004556 brain Anatomy 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000007954 hypoxia Effects 0.000 description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- -1 C - 4aIkoksylową Chemical group 0.000 description 8
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- 238000006243 chemical reaction Methods 0.000 description 6
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- 239000000902 placebo Substances 0.000 description 6
- 229940068196 placebo Drugs 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
- 229960004046 apomorphine Drugs 0.000 description 4
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- 230000002903 catalepsic effect Effects 0.000 description 4
- OYKIERKRPUDEIV-UHFFFAOYSA-N decane;hydrochloride Chemical compound Cl.CCCCCCCCCC OYKIERKRPUDEIV-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 208000013403 hyperactivity Diseases 0.000 description 4
- 230000001146 hypoxic effect Effects 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010042008 Stereotypy Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
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- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- PIMYDFDXAUVLON-UHFFFAOYSA-M chloro(triethyl)stannane Chemical compound CC[Sn](Cl)(CC)CC PIMYDFDXAUVLON-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- 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
- C07D491/10—Spiro-condensed systems
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU894094A HU204276B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
Publications (2)
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| PL291648A1 PL291648A1 (en) | 1992-06-01 |
| PL164662B1 true PL164662B1 (pl) | 1994-09-30 |
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| PL90286443A PL163899B1 (pl) | 1989-08-10 | 1990-08-10 | Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5] dekanu PL PL PL |
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| Application Number | Title | Priority Date | Filing Date |
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| PL90286443A PL163899B1 (pl) | 1989-08-10 | 1990-08-10 | Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5] dekanu PL PL PL |
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| EP (2) | EP0413516B1 (enExample) |
| JP (2) | JPH0381277A (enExample) |
| KR (2) | KR940000830B1 (enExample) |
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| AT (2) | ATE113951T1 (enExample) |
| AU (2) | AU621771B2 (enExample) |
| CA (2) | CA2023018C (enExample) |
| DD (2) | DD299431A5 (enExample) |
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| FI (1) | FI93456C (enExample) |
| HK (1) | HK118295A (enExample) |
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| IL (2) | IL95324A (enExample) |
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| NO (1) | NO903511L (enExample) |
| NZ (2) | NZ234843A (enExample) |
| PL (2) | PL164662B1 (enExample) |
| SG (1) | SG59864G (enExample) |
| YU (2) | YU150489A (enExample) |
| ZA (3) | ZA906299B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE152623T1 (de) * | 1986-12-17 | 1997-05-15 | Glaxo Group Ltd | Verwendung von heterozyklischen derivaten zur herstellung von arzneimitteln |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| US5852029A (en) * | 1990-04-10 | 1998-12-22 | Israel Institute For Biological Research | Aza spiro compounds acting on the cholinergic system with muscarinic agonist activity |
| EP0492020A1 (en) * | 1990-12-21 | 1992-07-01 | Merrell Dow Pharmaceuticals Inc. | Use of certain esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one and related compounds for treating cognitive disorders |
| GB9206989D0 (en) * | 1992-03-31 | 1992-05-13 | Glaxo Group Ltd | Chemical compounds |
| US5756743A (en) * | 1996-04-10 | 1998-05-26 | Hoechst Marion Roussel Inc. | Spiro cyclopent b!indole-piperidines! |
| US6100256A (en) * | 1996-12-02 | 2000-08-08 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptors antagonists for treating schizophrenic disorders |
| US6974825B1 (en) | 1996-12-20 | 2005-12-13 | Astrazeneca Canada Inc. | Compounds with analgesic effect |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| SE9904675D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE0101771D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101769D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101770D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101773D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| KR20030087248A (ko) * | 2002-05-08 | 2003-11-14 | (주)씨엔아이 | 온라인을 통한 상거래 기초항목의 설정기능을 갖는 상거래관리장치 |
| CN102459278A (zh) * | 2009-06-16 | 2012-05-16 | 默沙东公司 | 取代的-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮 |
| GB201416346D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
| GB201416352D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127065C (enExample) * | 1964-04-22 | |||
| CH601304A5 (enExample) * | 1974-02-12 | 1978-07-14 | Buskine Sa | |
| BE790675A (fr) * | 1971-10-29 | 1973-04-27 | Science Union & Cie | Nouveaux derives de l'oxa-1 diaza-3,8 spiro (4,5) decane |
| FR2615515B1 (fr) * | 1987-05-22 | 1989-06-30 | Adir | Nouveaux derives du spiro 4, 5 decane, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| HU204530B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
-
1989
- 1989-07-27 YU YU150489A patent/YU150489A/sh unknown
- 1989-08-10 HU HU894094A patent/HU204276B/hu not_active IP Right Cessation
- 1989-08-10 HU HU903233A patent/HU206677B/hu not_active IP Right Cessation
-
1990
- 1990-08-08 KR KR1019900012169A patent/KR940000830B1/ko not_active Expired - Fee Related
- 1990-08-08 KR KR1019900012168A patent/KR940002826B1/ko not_active Expired - Fee Related
- 1990-08-09 JP JP2209362A patent/JPH0381277A/ja active Pending
- 1990-08-09 IL IL9532490A patent/IL95324A/en not_active IP Right Cessation
- 1990-08-09 DE DE69008275T patent/DE69008275T2/de not_active Expired - Fee Related
- 1990-08-09 NZ NZ234843A patent/NZ234843A/en unknown
- 1990-08-09 NO NO90903511A patent/NO903511L/no unknown
- 1990-08-09 DE DE69014008T patent/DE69014008T2/de not_active Expired - Fee Related
- 1990-08-09 IS IS3612A patent/IS3612A7/is unknown
- 1990-08-09 ES ES90308783T patent/ES2052179T3/es not_active Expired - Lifetime
- 1990-08-09 IN IN687/CAL/90A patent/IN170979B/en unknown
- 1990-08-09 AT AT90308779T patent/ATE113951T1/de not_active IP Right Cessation
- 1990-08-09 EP EP90308783A patent/EP0413516B1/en not_active Expired - Lifetime
- 1990-08-09 ZA ZA906299A patent/ZA906299B/xx unknown
- 1990-08-09 DD DD90343359A patent/DD299431A5/de not_active IP Right Cessation
- 1990-08-09 AT AT9090308783T patent/ATE104671T1/de not_active IP Right Cessation
- 1990-08-09 ZA ZA906304A patent/ZA906304B/xx unknown
- 1990-08-09 CA CA002023018A patent/CA2023018C/en not_active Expired - Fee Related
- 1990-08-09 AU AU60803/90A patent/AU621771B2/en not_active Ceased
- 1990-08-09 YU YU154090A patent/YU154090A/sh unknown
- 1990-08-09 NZ NZ234846A patent/NZ234846A/en unknown
- 1990-08-09 AU AU60804/90A patent/AU621238B2/en not_active Ceased
- 1990-08-09 SG SG1995903969A patent/SG59864G/en unknown
- 1990-08-09 IL IL9532590A patent/IL95325A/en not_active IP Right Cessation
- 1990-08-09 ES ES90308779T patent/ES2063923T3/es not_active Expired - Lifetime
- 1990-08-09 EP EP90308779A patent/EP0412821B1/en not_active Expired - Lifetime
- 1990-08-09 DK DK90308783.1T patent/DK0413516T3/da active
- 1990-08-09 CA CA002023015A patent/CA2023015A1/en not_active Abandoned
- 1990-08-09 IE IE288590A patent/IE902885A1/en unknown
- 1990-08-09 DD DD90343354A patent/DD299428A5/de not_active IP Right Cessation
- 1990-08-09 ZA ZA906300A patent/ZA906300B/xx unknown
- 1990-08-09 JP JP2209363A patent/JPH0383985A/ja active Pending
- 1990-08-10 MY MYPI90001343A patent/MY107240A/en unknown
- 1990-08-10 US US07/566,279 patent/US5132309A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90291648A patent/PL164662B1/pl unknown
- 1990-08-10 FI FI903974A patent/FI93456C/fi not_active IP Right Cessation
- 1990-08-10 CN CN90106974A patent/CN1025031C/zh not_active Expired - Fee Related
- 1990-08-10 US US07/566,278 patent/US5132303A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90286443A patent/PL163899B1/pl unknown
-
1995
- 1995-07-20 HK HK118295A patent/HK118295A/en not_active IP Right Cessation
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