KR100704527B1 - Ｖｉｃ-디클로로산 플루오라이드의 제조 방법 - Google Patents
Ｖｉｃ-디클로로산 플루오라이드의 제조 방법 Download PDFInfo
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- KR100704527B1 KR100704527B1 KR1020027002651A KR20027002651A KR100704527B1 KR 100704527 B1 KR100704527 B1 KR 100704527B1 KR 1020027002651 A KR1020027002651 A KR 1020027002651A KR 20027002651 A KR20027002651 A KR 20027002651A KR 100704527 B1 KR100704527 B1 KR 100704527B1
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- 238000000034 method Methods 0.000 title claims abstract description 70
- 239000002253 acid Substances 0.000 title claims abstract description 21
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- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 64
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000011737 fluorine Substances 0.000 claims abstract description 44
- 239000007788 liquid Substances 0.000 claims abstract description 44
- 101100502522 Mus musculus Fcor gene Proteins 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 67
- 238000002360 preparation method Methods 0.000 claims description 47
- 238000003682 fluorination reaction Methods 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 38
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- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 37
- -1 fluoride compound Chemical class 0.000 claims description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 239000007791 liquid phase Substances 0.000 claims description 20
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- 238000010898 silica gel chromatography Methods 0.000 description 7
- DPBKQJJFNSNWMZ-UHFFFAOYSA-N 3,4-dichloro-2,2,3,4,4-pentafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(Cl)C(F)(F)Cl DPBKQJJFNSNWMZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 238000000197 pyrolysis Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000005979 thermal decomposition reaction Methods 0.000 description 6
- UCCWJJZPOSPPIC-UHFFFAOYSA-N COOCF Chemical compound COOCF UCCWJJZPOSPPIC-UHFFFAOYSA-N 0.000 description 5
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 5
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- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 5
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 4
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
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- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 3
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 3
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- CJXGPJZUDUOZDX-UHFFFAOYSA-N fluoromethanone Chemical group F[C]=O CJXGPJZUDUOZDX-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
- C07C59/135—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24615499 | 1999-08-31 | ||
| JPJP-P-1999-00246154 | 1999-08-31 | ||
| JP2000211722 | 2000-07-12 | ||
| JPJP-P-2000-00211722 | 2000-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20020025244A KR20020025244A (ko) | 2002-04-03 |
| KR100704527B1 true KR100704527B1 (ko) | 2007-04-10 |
Family
ID=26537593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027002651A Expired - Lifetime KR100704527B1 (ko) | 1999-08-31 | 2000-08-30 | Ｖｉｃ-디클로로산 플루오라이드의 제조 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6833477B2 (https=) |
| EP (1) | EP1208075B1 (https=) |
| JP (1) | JP4626118B2 (https=) |
| KR (1) | KR100704527B1 (https=) |
| CN (1) | CN1167662C (https=) |
| AT (1) | ATE278657T1 (https=) |
| AU (1) | AU6866000A (https=) |
| CA (1) | CA2381351C (https=) |
| DE (1) | DE60014673T2 (https=) |
| RU (1) | RU2252210C2 (https=) |
| WO (1) | WO2001016085A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2290020T3 (es) | 1999-03-23 | 2008-02-16 | Asahi Glass Company Ltd. | Procedimiento para producir un compuesto de fluor por medio de una fluoracion en fase liquida. |
| AU2398601A (en) * | 1999-12-20 | 2001-07-03 | Asahi Glass Company Limited | Process for producing a fluoride compound |
| JP4956856B2 (ja) * | 1999-12-20 | 2012-06-20 | 旭硝子株式会社 | フルオリド化合物の製造方法 |
| JP4802438B2 (ja) * | 2000-06-02 | 2011-10-26 | 旭硝子株式会社 | 熱分解反応による不飽和化合物の製造方法 |
| EP1300386B1 (en) | 2000-07-11 | 2007-09-19 | Asahi Glass Company, Limited | Method for producing fluorine-containing compound |
| AU2001288099A1 (en) * | 2000-09-27 | 2002-04-08 | Asahi Glass Company, Limited | Process for producing fluorinated polyvalent carbonyl compound |
| CN1242979C (zh) | 2000-09-27 | 2006-02-22 | 旭硝子株式会社 | 含氟酯化合物的制造方法 |
| JP4492121B2 (ja) * | 2001-10-30 | 2010-06-30 | 旭硝子株式会社 | フルオロスルホニル基含有化合物および該化合物から誘導される化合物の製造方法 |
| US7247757B2 (en) | 2004-10-06 | 2007-07-24 | Fujifilm Corporation | Method of producing a fluorine-containing vinyl ether compound |
| CN100338012C (zh) * | 2005-11-07 | 2007-09-19 | 上海泰卓科技有限公司 | 一种含氟酰氟类化合物的处理方法 |
| KR101397113B1 (ko) | 2006-10-03 | 2014-05-19 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| JP2009203172A (ja) * | 2008-02-26 | 2009-09-10 | Fujifilm Corp | パーフルオロ多官能ビニルエーテル化合物の製造方法 |
| CN114085142B (zh) * | 2021-10-28 | 2024-08-20 | 浙江诺亚氟化工有限公司 | 一种含氟醚类化合物气相氧化裂解反应合成酰氟类化合物的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02311438A (ja) * | 1989-05-24 | 1990-12-27 | Asahi Glass Co Ltd | 新規含フッ素化合物，その製造方法及び用途 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900372A (en) | 1974-09-16 | 1975-08-19 | Phillips Petroleum Co | Recycle of acyl fluoride and electrochemical fluorination of esters |
| JPS54135722A (en) * | 1978-04-12 | 1979-10-22 | Toyo Soda Mfg Co Ltd | Preparation of fluorine-containing ether |
| US4420638A (en) * | 1982-03-02 | 1983-12-13 | E. I. Du Pont De Nemours And Company | Fluorinated ether-ketones |
| US5332790A (en) | 1988-09-28 | 1994-07-26 | Exfluor Research Corporation | Liquid-phase fluorination |
| US5322904A (en) | 1988-09-28 | 1994-06-21 | Exfluor Research Corporation | Liquid-phase fluorination |
| US5093432A (en) | 1988-09-28 | 1992-03-03 | Exfluor Research Corporation | Liquid phase fluorination |
| RU2043328C1 (ru) * | 1993-01-11 | 1995-09-10 | Российский научный центр "Прикладная химия" | Способ получения мономеров |
| US5466877A (en) * | 1994-03-15 | 1995-11-14 | Minnesota Mining And Manufacturing Company | Process for converting perfluorinated esters to perfluorinated acyl fluorides and/or ketones |
| US5658785A (en) * | 1994-06-06 | 1997-08-19 | Children's Hospital, Inc. | Adeno-associated virus materials and methods |
| MX9708008A (es) * | 1995-04-19 | 1998-03-31 | Polymun Scient Immunbio Forsch | Anticuerpos monoclonales contra vih-1 y vacunas hechas de los mismos. |
| JP2000505082A (ja) * | 1996-02-23 | 2000-04-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジハロジフルオロメタンおよびその同族体の製造方法 |
| US5846946A (en) * | 1996-06-14 | 1998-12-08 | Pasteur Merieux Serums Et Vaccins | Compositions and methods for administering Borrelia DNA |
| US6077662A (en) * | 1996-11-27 | 2000-06-20 | Emory University | Virus-like particles, methods and immunogenic compositions |
| US6054312A (en) * | 1997-08-29 | 2000-04-25 | Selective Genetics, Inc. | Receptor-mediated gene delivery using bacteriophage vectors |
| US6156952A (en) * | 1998-04-09 | 2000-12-05 | Constituent Institution Of The University Of Maryland System | HIV transgenic animals and uses therefor |
| AUPP349698A0 (en) * | 1998-05-13 | 1998-06-04 | Altronic Distributors Pty Ltd | Mounting assembly |
| JP2000154158A (ja) * | 1998-11-18 | 2000-06-06 | Asahi Glass Co Ltd | 含フッ素化合物およびその製法 |
| JP2001139509A (ja) * | 1999-08-31 | 2001-05-22 | Asahi Glass Co Ltd | 熱分解反応による不飽和化合物の製造方法 |
| US6255535B1 (en) | 1999-12-22 | 2001-07-03 | Dyneon Llc | Fluorine containing allylethers and higher homologs |
-
2000
- 2000-08-30 RU RU2002107994/04A patent/RU2252210C2/ru active
- 2000-08-30 JP JP2001519655A patent/JP4626118B2/ja not_active Expired - Lifetime
- 2000-08-30 AT AT00956818T patent/ATE278657T1/de not_active IP Right Cessation
- 2000-08-30 CN CNB008119902A patent/CN1167662C/zh not_active Expired - Lifetime
- 2000-08-30 AU AU68660/00A patent/AU6866000A/en not_active Abandoned
- 2000-08-30 KR KR1020027002651A patent/KR100704527B1/ko not_active Expired - Lifetime
- 2000-08-30 WO PCT/JP2000/005888 patent/WO2001016085A1/en not_active Ceased
- 2000-08-30 CA CA002381351A patent/CA2381351C/en not_active Expired - Fee Related
- 2000-08-30 DE DE60014673T patent/DE60014673T2/de not_active Expired - Lifetime
- 2000-08-30 EP EP00956818A patent/EP1208075B1/en not_active Expired - Lifetime
-
2002
- 2002-02-28 US US10/084,506 patent/US6833477B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02311438A (ja) * | 1989-05-24 | 1990-12-27 | Asahi Glass Co Ltd | 新規含フッ素化合物，その製造方法及び用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60014673D1 (de) | 2004-11-11 |
| CN1167662C (zh) | 2004-09-22 |
| CN1371353A (zh) | 2002-09-25 |
| US6833477B2 (en) | 2004-12-21 |
| AU6866000A (en) | 2001-03-26 |
| KR20020025244A (ko) | 2002-04-03 |
| US20020107358A1 (en) | 2002-08-08 |
| JP2003508374A (ja) | 2003-03-04 |
| WO2001016085A1 (en) | 2001-03-08 |
| RU2252210C2 (ru) | 2005-05-20 |
| JP4626118B2 (ja) | 2011-02-02 |
| EP1208075B1 (en) | 2004-10-06 |
| CA2381351C (en) | 2009-11-17 |
| ATE278657T1 (de) | 2004-10-15 |
| EP1208075A1 (en) | 2002-05-29 |
| DE60014673T2 (de) | 2005-02-17 |
| CA2381351A1 (en) | 2001-03-08 |
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