SK281622B6 - Spôsob prípravy 8-{4'-[4''-(pyrimidin-2'''-yl)-piperazin-1''- -yl]-butyl}-8-azaspiro[4,5]dekan-7,9-diónu a jeho hydrochloridov - Google Patents
Spôsob prípravy 8-{4'-[4''-(pyrimidin-2'''-yl)-piperazin-1''- -yl]-butyl}-8-azaspiro[4,5]dekan-7,9-diónu a jeho hydrochloridov Download PDFInfo
- Publication number
- SK281622B6 SK281622B6 SK861-94A SK86194A SK281622B6 SK 281622 B6 SK281622 B6 SK 281622B6 SK 86194 A SK86194 A SK 86194A SK 281622 B6 SK281622 B6 SK 281622B6
- Authority
- SK
- Slovakia
- Prior art keywords
- spiro
- aza
- dione
- decane
- pyrimidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000003840 hydrochlorides Chemical class 0.000 title abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 12
- 239000000725 suspension Substances 0.000 claims abstract description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 83
- 239000000047 product Substances 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 238000002844 melting Methods 0.000 claims description 22
- 230000008018 melting Effects 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000356 contaminant Substances 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 9
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- YRTHJMQKDCXPAY-UHFFFAOYSA-N azaspirodecanedione Chemical compound C1C(=O)NC(=O)CC11CCCC1 YRTHJMQKDCXPAY-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000003880 polar aprotic solvent Substances 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- URVJUARKBQLSGJ-UHFFFAOYSA-N 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)but-2-ynyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)N(CC#CCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 URVJUARKBQLSGJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000002585 base Substances 0.000 description 20
- 230000004048 modification Effects 0.000 description 18
- 238000012986 modification Methods 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- -1 nitrile compound Chemical class 0.000 description 4
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960002495 buspirone Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 2
- YDQAUSHJSHIVAD-UHFFFAOYSA-N 4-(4-pyrimidin-2-ylpiperazin-1-yl)butan-1-amine Chemical compound C1CN(CCCCN)CCN1C1=NC=CC=N1 YDQAUSHJSHIVAD-UHFFFAOYSA-N 0.000 description 2
- BCNBRBQCDHLCBD-UHFFFAOYSA-N 8-(4-chlorobutyl)-8-azaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)N(CCCCCl)C(=O)CC11CCCC1 BCNBRBQCDHLCBD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229960001768 buspirone hydrochloride Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- XBVZKHPTGUWNEH-UHFFFAOYSA-N 2-[4-(4-chlorobutyl)piperazin-1-yl]pyrimidine Chemical compound C1CN(CCCCCl)CCN1C1=NC=CC=N1 XBVZKHPTGUWNEH-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DOQLCJMCQWQQHK-UHFFFAOYSA-N 4-chlorobutanal Chemical compound ClCCCC=O DOQLCJMCQWQQHK-UHFFFAOYSA-N 0.000 description 1
- GFWLMILMVMCJDI-UHFFFAOYSA-N 8-oxaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)OC(=O)CC11CCCC1 GFWLMILMVMCJDI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- AXMNGEUJXLXFRY-UHFFFAOYSA-N azaspirodecane Chemical compound C1CCCC21CCNCC2 AXMNGEUJXLXFRY-UHFFFAOYSA-N 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Anesthesiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9302040A HU217129B (hu) | 1993-07-16 | 1993-07-16 | Eljárás nagy tisztaságú buspiron gyógyászati hatóanyag előállítására |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK86194A3 SK86194A3 (en) | 1995-03-08 |
| SK281622B6 true SK281622B6 (sk) | 2001-05-10 |
Family
ID=10983790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK861-94A SK281622B6 (sk) | 1993-07-16 | 1994-07-15 | Spôsob prípravy 8-{4'-[4''-(pyrimidin-2'''-yl)-piperazin-1''- -yl]-butyl}-8-azaspiro[4,5]dekan-7,9-diónu a jeho hydrochloridov |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5473072A (ru) |
| EP (1) | EP0634411B1 (ru) |
| JP (1) | JPH07165755A (ru) |
| KR (1) | KR950003287A (ru) |
| AT (1) | ATE180480T1 (ru) |
| BG (1) | BG98904A (ru) |
| CA (1) | CA2128164A1 (ru) |
| CZ (1) | CZ287531B6 (ru) |
| DE (1) | DE59408299D1 (ru) |
| ES (1) | ES2082722B1 (ru) |
| FR (1) | FR2709128B1 (ru) |
| GB (1) | GB2280185B (ru) |
| HR (1) | HRP940408B1 (ru) |
| HU (1) | HU217129B (ru) |
| IT (1) | IT1271677B (ru) |
| PL (1) | PL176708B1 (ru) |
| RU (1) | RU2131875C1 (ru) |
| SK (1) | SK281622B6 (ru) |
| UA (1) | UA44687C2 (ru) |
| ZA (1) | ZA945210B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2146593A1 (en) * | 1994-05-05 | 1995-11-06 | Jack Melton | Large-scale process for azapirone synthesis |
| US20040127501A1 (en) * | 2002-09-24 | 2004-07-01 | Zhengming Chen | Therapeutic agents useful for treating pain |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1943024B2 (de) * | 1969-08-23 | 1972-12-21 | Metallgesellschaft Ag, 6000 Frankfurt | Vorrichtung zur abdichtung von end-windkaesten von wanderrosten |
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| JPS6310760A (ja) * | 1986-07-01 | 1988-01-18 | Sumitomo Pharmaceut Co Ltd | イミド誘導体の新規製造法 |
| JPS6310786A (ja) * | 1986-07-01 | 1988-01-18 | Sumitomo Pharmaceut Co Ltd | 新規イミド誘導体およびその製造法 |
| CH677924A5 (ru) * | 1987-02-25 | 1991-07-15 | Egyt Gyogyszervegyeszeti Gyar | |
| US4810789A (en) * | 1987-08-28 | 1989-03-07 | Bristol-Myers Company | Process for buspirone hydrochloride polymorphic crystalline form conversion |
| US5015646A (en) * | 1987-08-28 | 1991-05-14 | Bristol-Myers Squibb Co. | Pharmaceutically useful polymorphic modification of buspirone |
| US5130315A (en) * | 1991-01-10 | 1992-07-14 | Raymond R. Wittekind | 1-piperazinyl-2-butenes and -2-butynes |
-
1993
- 1993-07-16 HU HU9302040A patent/HU217129B/hu unknown
-
1994
- 1994-07-12 FR FR9408621A patent/FR2709128B1/fr not_active Expired - Fee Related
- 1994-07-14 CZ CZ19941709A patent/CZ287531B6/cs not_active IP Right Cessation
- 1994-07-14 US US08/274,848 patent/US5473072A/en not_active Expired - Lifetime
- 1994-07-14 RU RU94026281A patent/RU2131875C1/ru not_active IP Right Cessation
- 1994-07-15 EP EP94111037A patent/EP0634411B1/de not_active Expired - Lifetime
- 1994-07-15 AT AT94111037T patent/ATE180480T1/de active
- 1994-07-15 GB GB9414325A patent/GB2280185B/en not_active Expired - Fee Related
- 1994-07-15 DE DE59408299T patent/DE59408299D1/de not_active Expired - Fee Related
- 1994-07-15 KR KR1019940017063A patent/KR950003287A/ko active IP Right Grant
- 1994-07-15 UA UA94075638A patent/UA44687C2/uk unknown
- 1994-07-15 SK SK861-94A patent/SK281622B6/sk not_active IP Right Cessation
- 1994-07-15 ZA ZA945210A patent/ZA945210B/xx unknown
- 1994-07-15 PL PL94304313A patent/PL176708B1/pl not_active IP Right Cessation
- 1994-07-15 CA CA002128164A patent/CA2128164A1/en not_active Abandoned
- 1994-07-15 HR HRP9302040A patent/HRP940408B1/xx not_active IP Right Cessation
- 1994-07-15 BG BG98904A patent/BG98904A/bg unknown
- 1994-07-15 ES ES09401543A patent/ES2082722B1/es not_active Expired - Lifetime
- 1994-07-18 IT ITMI941492A patent/IT1271677B/it active IP Right Grant
- 1994-07-18 JP JP6165115A patent/JPH07165755A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HRP940408A2 (en) | 1996-10-31 |
| US5473072A (en) | 1995-12-05 |
| PL176708B1 (pl) | 1999-07-30 |
| EP0634411B1 (de) | 1999-05-26 |
| BG98904A (bg) | 1995-05-31 |
| FR2709128B1 (fr) | 1996-02-23 |
| CZ170994A3 (en) | 1995-04-12 |
| DE59408299D1 (de) | 1999-07-01 |
| GB2280185B (en) | 1997-04-16 |
| FR2709128A1 (fr) | 1995-02-24 |
| GB9414325D0 (en) | 1994-09-07 |
| ZA945210B (en) | 1996-01-15 |
| RU2131875C1 (ru) | 1999-06-20 |
| HU217129B (hu) | 1999-11-29 |
| ATE180480T1 (de) | 1999-06-15 |
| EP0634411A1 (de) | 1995-01-18 |
| GB2280185A (en) | 1995-01-25 |
| ITMI941492A1 (it) | 1996-01-18 |
| PL304313A1 (en) | 1995-01-23 |
| CZ287531B6 (en) | 2000-12-13 |
| IT1271677B (it) | 1997-06-04 |
| KR950003287A (ko) | 1995-02-16 |
| ES2082722B1 (es) | 1996-10-01 |
| UA44687C2 (uk) | 2002-03-15 |
| CA2128164A1 (en) | 1995-01-17 |
| SK86194A3 (en) | 1995-03-08 |
| HRP940408B1 (en) | 2000-02-29 |
| HUT69720A (en) | 1995-09-28 |
| ITMI941492A0 (it) | 1994-07-18 |
| HU9302040D0 (en) | 1993-10-28 |
| RU94026281A (ru) | 1996-05-27 |
| JPH07165755A (ja) | 1995-06-27 |
| ES2082722A1 (es) | 1996-03-16 |
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Effective date: 20100715 |