KR920004337A - 비페닐카르보니트릴의 제조방법 - Google Patents
비페닐카르보니트릴의 제조방법 Download PDFInfo
- Publication number
- KR920004337A KR920004337A KR1019910013873A KR910013873A KR920004337A KR 920004337 A KR920004337 A KR 920004337A KR 1019910013873 A KR1019910013873 A KR 1019910013873A KR 910013873 A KR910013873 A KR 910013873A KR 920004337 A KR920004337 A KR 920004337A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- palladium
- nickel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 14
- -1 bromo, iodo Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 239000003999 initiator Substances 0.000 claims 3
- 231100000252 nontoxic Toxicity 0.000 claims 3
- 230000003000 nontoxic effect Effects 0.000 claims 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- BRTALTYTFFNPAC-UHFFFAOYSA-N boroxin Chemical group B1OBOBO1 BRTALTYTFFNPAC-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 238000009938 salting Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims 1
- 150000001639 boron compounds Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 claims 1
- KFBKRCXOTTUAFS-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KFBKRCXOTTUAFS-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Turning (AREA)
- Glass Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Air Bags (AREA)
- Electrotherapy Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9017482.2 | 1990-08-09 | ||
| GB909017482A GB9017482D0 (en) | 1990-08-09 | 1990-08-09 | Manufacturing process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920004337A true KR920004337A (ko) | 1992-03-27 |
Family
ID=10680408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910013873A Withdrawn KR920004337A (ko) | 1990-08-09 | 1991-08-08 | 비페닐카르보니트릴의 제조방법 |
Country Status (23)
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE117294T1 (de) * | 1989-08-11 | 1995-02-15 | Ici Plc | Chinolin-derivate, verfahren zu ihrer herstellung und ihre anwendung als arzneimittel. |
| DE4132632A1 (de) * | 1991-10-01 | 1993-04-08 | Bayer Ag | Substituierte imidazolyl-propensaeurederivate |
| DE4132633A1 (de) * | 1991-10-01 | 1993-04-08 | Bayer Ag | Cyclisch substituierte imidazolyl-propensaeurederivate |
| DE4132631A1 (de) * | 1991-10-01 | 1993-04-08 | Bayer Ag | Imidazolyl-propensaeurederivate |
| US5310928A (en) * | 1991-11-18 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Process for preparing biphenyltetrazole compounds |
| US5206374A (en) * | 1991-11-18 | 1993-04-27 | E. I. Du Pont De Nemours And Company | Process for preparing tetrazolylphenylboronic acid intermediates |
| FR2688507B1 (fr) * | 1992-03-16 | 1994-05-06 | Synthelabo | Derives de l'acide tetrazolylbenzeneboronique, leur preparation et leur utilisation comme intermediaires de synthese. |
| FR2689887B1 (fr) * | 1992-04-13 | 1995-06-23 | Sanofi Elf | Procede de preparation d'un derive de biphenyle. |
| FR2696746B1 (fr) * | 1992-10-12 | 1994-11-18 | Synthelabo | Dérivés de l'acide benzèneborinique, leur préparation et leur utilisation comme intermédiaires de synthèse. |
| DE4423061C1 (de) | 1994-07-01 | 1996-01-18 | Hoechst Ag | Verfahren zur Herstellung von Biphenylen mit Palladacyclen als Katalysatoren |
| DE4426671A1 (de) * | 1994-07-28 | 1996-02-01 | Hoechst Ag | Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten |
| KR100354802B1 (ko) * | 1994-10-20 | 2002-12-26 | 한국화학연구원 | 테트라졸유도체의제조방법 |
| JP2928982B2 (ja) | 1994-10-27 | 1999-08-03 | 住化ファインケム株式会社 | ４’−ブロモメチル−２−シアノビフェニルの製造法 |
| DE19620023C2 (de) * | 1996-05-17 | 2001-03-08 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane |
| US5922898A (en) * | 1997-04-08 | 1999-07-13 | Catalytica Pharmaceuticals, Inc. | Process for preparing biaryl compounds |
| US6194599B1 (en) | 1997-04-08 | 2001-02-27 | Catalytica, Inc. | Process for preparing biaryl compounds |
| JP2002506836A (ja) | 1998-03-18 | 2002-03-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | パラジウム触媒によるカップリング反応 |
| US6962999B2 (en) | 2001-07-25 | 2005-11-08 | Pharmacore, Inc. | Process for preparing unsymmetrical biaryls and alkylated aromatic compounds from arylnitriles |
| DE10211597A1 (de) | 2002-03-15 | 2003-10-02 | Merck Patent Gmbh | Verfahren zur Herstellung von Ringverbindungen |
| ATE321039T1 (de) | 2002-04-29 | 2006-04-15 | Teva Pharma | Verfahren zur herstellung von losartan und losartan-kaliumsalz |
| PT1535901E (pt) | 2002-06-12 | 2008-04-10 | Sumitomo Chemical Co | Processo para a produção de 4'-bromometil-2-cianobifenilo |
| US7105467B2 (en) | 2003-07-08 | 2006-09-12 | Pharmacore, Inc. | Nickel catalyzed cross-coupling reactions between organomagnesium compounds and anisole derivatives |
| US7105707B2 (en) | 2003-12-17 | 2006-09-12 | Pharmacore, Inc. | Process for preparing alkynyl-substituted aromatic and heterocyclic compounds |
| JP2006151946A (ja) * | 2004-04-30 | 2006-06-15 | Konishi Kagaku Ind Co Ltd | ジアリール誘導体の製造方法 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2393885T7 (es) | 2007-06-04 | 2014-01-30 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| MX2012002301A (es) * | 2009-08-31 | 2012-03-29 | Bayer Cropscience Ag | Procedimiento de tetraarilborato para la preparacion de bifenilos sustituidos. |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| EA201592263A1 (ru) | 2013-06-05 | 2016-05-31 | Синерджи Фармасьютикалз, Инк. | Ультрачистые агонисты гуанилатциклазы c, способ их получения и использования |
| JP5975081B2 (ja) * | 2013-09-30 | 2016-08-23 | ダイキン工業株式会社 | 含フッ素ビアリール化合物の製造方法 |
| CN119677720A (zh) | 2021-11-02 | 2025-03-21 | 弗拉雷治疗公司 | Pparg反向激动剂及其用途 |
| CN117623932A (zh) * | 2023-11-30 | 2024-03-01 | 江苏康恒化工有限公司 | 中间体2，2’-二硝基联苯的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1334092C (en) * | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| EP0395666B1 (en) * | 1987-10-19 | 1994-05-04 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Laterally cyano- and fluoro-substituted terphenyls |
| CA1338238C (en) * | 1988-01-07 | 1996-04-09 | David John Carini | Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids |
| ATE117294T1 (de) * | 1989-08-11 | 1995-02-15 | Ici Plc | Chinolin-derivate, verfahren zu ihrer herstellung und ihre anwendung als arzneimittel. |
-
1990
- 1990-08-09 GB GB909017482A patent/GB9017482D0/en active Pending
-
1991
- 1991-07-15 ZW ZW95/91A patent/ZW9591A1/xx unknown
- 1991-07-16 IL IL98862A patent/IL98862A0/xx unknown
- 1991-07-16 AU AU80436/91A patent/AU646473B2/en not_active Ceased
- 1991-07-16 ZA ZA915566A patent/ZA915566B/xx unknown
- 1991-07-16 GB GB919115244A patent/GB9115244D0/en active Pending
- 1991-07-18 CA CA002047369A patent/CA2047369A1/en not_active Abandoned
- 1991-07-18 NZ NZ239026A patent/NZ239026A/en unknown
- 1991-07-24 HU HU912481A patent/HU207841B/hu not_active IP Right Cessation
- 1991-07-29 CN CN91105206A patent/CN1059516A/zh active Pending
- 1991-07-30 FI FI913640A patent/FI913640A7/fi unknown
- 1991-08-02 CS CS912413A patent/CS241391A3/cs unknown
- 1991-08-05 EP EP91307184A patent/EP0470795B2/en not_active Expired - Lifetime
- 1991-08-05 AT AT91307184T patent/ATE117672T1/de active
- 1991-08-05 ES ES91307184T patent/ES2067159T3/es not_active Expired - Lifetime
- 1991-08-05 DE DE69106977T patent/DE69106977T3/de not_active Expired - Fee Related
- 1991-08-08 RU SU915001352A patent/RU2026285C1/ru active
- 1991-08-08 KR KR1019910013873A patent/KR920004337A/ko not_active Withdrawn
- 1991-08-08 PL PL29137091A patent/PL291370A1/xx unknown
- 1991-08-08 PT PT98608A patent/PT98608A/pt not_active Application Discontinuation
- 1991-08-08 JP JP3199442A patent/JP3001298B2/ja not_active Expired - Fee Related
- 1991-08-08 NO NO913086A patent/NO174502B/no unknown
- 1991-08-09 YU YU137891A patent/YU137891A/sh unknown
- 1991-08-12 TW TW080106352A patent/TW198710B/zh active
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