FI120347B - Uusi menetelmä di-isopinokamfeyyliklooriboraanin valmistamiseksi ja menetelmä prokiraalisen ketonin pelkistämiseksi - Google Patents
Uusi menetelmä di-isopinokamfeyyliklooriboraanin valmistamiseksi ja menetelmä prokiraalisen ketonin pelkistämiseksi Download PDFInfo
- Publication number
- FI120347B FI120347B FI970564A FI970564A FI120347B FI 120347 B FI120347 B FI 120347B FI 970564 A FI970564 A FI 970564A FI 970564 A FI970564 A FI 970564A FI 120347 B FI120347 B FI 120347B
- Authority
- FI
- Finland
- Prior art keywords
- pinene
- process according
- optical purity
- preparation
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000002576 ketones Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims abstract description 35
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims abstract description 20
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000003287 optical effect Effects 0.000 claims abstract description 15
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- GRWFGVWFFZKLTI-RKDXNWHRSA-N (+)-α-pinene Chemical group CC1=CC[C@H]2C(C)(C)[C@@H]1C2 GRWFGVWFFZKLTI-RKDXNWHRSA-N 0.000 claims description 5
- -1 7-chloro-2-quinolinyl Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane of uncertain configuration Natural products CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 238000002955 isolation Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 14
- UOALEFQKAOQICC-UHFFFAOYSA-N chloroborane Chemical compound ClB UOALEFQKAOQICC-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229930006720 (-)-alpha-pinene Natural products 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- REPVLJRCJUVQFA-KZVJFYERSA-N (1r,3s,4s,5s)-4,6,6-trimethylbicyclo[3.1.1]heptan-3-ol Chemical compound C1[C@H](O)[C@@H](C)[C@H]2C(C)(C)[C@@H]1C2 REPVLJRCJUVQFA-KZVJFYERSA-N 0.000 description 1
- JQYYUWHWGCJWTN-UHFFFAOYSA-N 2-ethoxyoxolane Chemical compound CCOC1CCCO1 JQYYUWHWGCJWTN-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- INCCMBMMWVKEGJ-UHFFFAOYSA-N 4-methyl-1,3-dioxane Chemical compound CC1CCOCO1 INCCMBMMWVKEGJ-UHFFFAOYSA-N 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical class CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- DNXFCUINRMVXSF-UHFFFAOYSA-N chloroboron;methylsulfanylmethane Chemical compound Cl[B].CSC DNXFCUINRMVXSF-UHFFFAOYSA-N 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Detergent Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
- Lock And Its Accessories (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/289,077 US5545758A (en) | 1994-08-11 | 1994-08-11 | Process for the preparation of diisopinocampheylchloroborane |
| US28907794 | 1994-08-11 | ||
| PCT/US1995/009921 WO1996005206A1 (en) | 1994-08-11 | 1995-08-07 | Novel process for the preparation of diisopinocampheylchloroborane |
| US9509921 | 1995-08-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970564A0 FI970564A0 (fi) | 1997-02-10 |
| FI970564A FI970564A (fi) | 1997-02-10 |
| FI120347B true FI120347B (fi) | 2009-09-30 |
Family
ID=23109960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970564A FI120347B (fi) | 1994-08-11 | 1997-02-10 | Uusi menetelmä di-isopinokamfeyyliklooriboraanin valmistamiseksi ja menetelmä prokiraalisen ketonin pelkistämiseksi |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US5545758A (ko) |
| EP (1) | EP0775146B1 (ko) |
| JP (1) | JPH10504307A (ko) |
| KR (1) | KR100355916B1 (ko) |
| CN (2) | CN1051087C (ko) |
| AT (1) | ATE219087T1 (ko) |
| AU (1) | AU693588B2 (ko) |
| BR (1) | BR9508578A (ko) |
| CA (1) | CA2195776C (ko) |
| CZ (2) | CZ294311B6 (ko) |
| DE (1) | DE69527070T2 (ko) |
| DK (1) | DK0775146T3 (ko) |
| ES (1) | ES2176335T3 (ko) |
| FI (1) | FI120347B (ko) |
| HU (1) | HU215183B (ko) |
| MX (1) | MX9701087A (ko) |
| NZ (1) | NZ291101A (ko) |
| PT (1) | PT775146E (ko) |
| RO (1) | RO115882B1 (ko) |
| RU (1) | RU2150472C1 (ko) |
| SI (1) | SI0775146T1 (ko) |
| UA (1) | UA46741C2 (ko) |
| WO (1) | WO1996005206A1 (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0211204A (pt) * | 2001-07-17 | 2004-07-13 | Upjohn Co | Processo e intermediários para preparar latanoprost |
| WO2006021974A1 (en) * | 2004-08-23 | 2006-03-02 | Morepen Laboratories Limited | A process for synthesizing diol (viii)-an intermediate of montelukast sodium |
| US20060223999A1 (en) * | 2006-05-10 | 2006-10-05 | Chemagis Ltd. | Process for preparing montelukast and precursors thereof |
| CN101225089B (zh) * | 2007-01-17 | 2011-06-15 | 上海迪赛诺医药发展有限公司 | 制备二异松蒎基氯甲硼烷的方法 |
| KR20100061571A (ko) | 2007-09-28 | 2010-06-07 | 코덱시스, 인코포레이티드 | 케토리덕타제 폴리펩티드 및 이의 용도 |
| US20100055052A1 (en) * | 2008-08-26 | 2010-03-04 | James Albert Berta | Processing System for Oral Care Compositions |
| CN101525344B (zh) * | 2009-04-09 | 2011-10-05 | 霸州市路德精细化工有限公司 | 异松蒎基硼烷氯化物的制备方法 |
| CN103030658B (zh) * | 2012-06-29 | 2015-08-19 | 山东威智医药工业有限公司 | 二异松蒎基氯甲硼烷的工业化生产方法 |
| CN103601708B (zh) * | 2013-12-11 | 2015-06-17 | 武汉武药科技有限公司 | 一种前列素药物杂质的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043479A (en) * | 1986-08-29 | 1991-08-27 | Aldrich Chemical Company, Inc. | Chemically and optically pure diisopinocampheylhaloboranes |
| CA2050820A1 (en) * | 1990-09-24 | 1992-03-25 | Pamela M. Simpson | In-situ preparation of diisopinocamphenyl chloroborane |
| US5159116A (en) * | 1991-07-15 | 1992-10-27 | Aldrich Chemical Company, Inc. | Chemically and optically pure B-halodiiso-2-ethylapopinocampheylboranes |
| US5220072A (en) * | 1991-07-15 | 1993-06-15 | Aldrich Chemical Co., Inc. | Process of synthesizing chemically and optically pure B-halodiiso-2-ethylapopinocampheylboranes |
| US5270324A (en) * | 1992-04-10 | 1993-12-14 | Merck Frosst Canada, Inc. | Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists |
| US5220077A (en) * | 1992-08-19 | 1993-06-15 | Vista Chemical Company | Alkoxylation process |
-
1994
- 1994-08-11 US US08/289,077 patent/US5545758A/en not_active Expired - Lifetime
-
1995
- 1995-08-07 BR BR9508578A patent/BR9508578A/pt not_active IP Right Cessation
- 1995-08-07 DK DK95928320T patent/DK0775146T3/da active
- 1995-08-07 DE DE69527070T patent/DE69527070T2/de not_active Expired - Lifetime
- 1995-08-07 JP JP8507416A patent/JPH10504307A/ja not_active Ceased
- 1995-08-07 RO RO97-00268A patent/RO115882B1/ro unknown
- 1995-08-07 NZ NZ291101A patent/NZ291101A/en not_active IP Right Cessation
- 1995-08-07 HU HU9701953A patent/HU215183B/hu not_active IP Right Cessation
- 1995-08-07 EP EP95928320A patent/EP0775146B1/en not_active Expired - Lifetime
- 1995-08-07 ES ES95928320T patent/ES2176335T3/es not_active Expired - Lifetime
- 1995-08-07 RU RU97103951/04A patent/RU2150472C1/ru not_active IP Right Cessation
- 1995-08-07 CZ CZ19993445A patent/CZ294311B6/cs not_active IP Right Cessation
- 1995-08-07 CZ CZ1997387A patent/CZ286602B6/cs not_active IP Right Cessation
- 1995-08-07 CN CN95195485A patent/CN1051087C/zh not_active Expired - Fee Related
- 1995-08-07 AT AT95928320T patent/ATE219087T1/de active
- 1995-08-07 CA CA002195776A patent/CA2195776C/en not_active Expired - Fee Related
- 1995-08-07 WO PCT/US1995/009921 patent/WO1996005206A1/en active IP Right Grant
- 1995-08-07 KR KR1019970700854A patent/KR100355916B1/ko not_active IP Right Cessation
- 1995-08-07 UA UA97031025A patent/UA46741C2/uk unknown
- 1995-08-07 PT PT95928320T patent/PT775146E/pt unknown
- 1995-08-07 AU AU32135/95A patent/AU693588B2/en not_active Ceased
- 1995-08-07 SI SI9530597T patent/SI0775146T1/xx unknown
- 1995-08-07 MX MX9701087A patent/MX9701087A/es unknown
-
1996
- 1996-01-16 US US08/586,037 patent/US5693816A/en not_active Expired - Lifetime
-
1997
- 1997-02-10 FI FI970564A patent/FI120347B/fi not_active IP Right Cessation
-
1999
- 1999-06-28 CN CN99108855A patent/CN1122039C/zh not_active Expired - Fee Related
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