KR20020043565A - 조성물에서의 오메프라졸 이성질체 비율의ｆｔ－ｒａｍａｎ 분광학적 측정 - Google Patents
조성물에서의 오메프라졸 이성질체 비율의ｆｔ－ｒａｍａｎ 분광학적 측정 Download PDFInfo
- Publication number
- KR20020043565A KR20020043565A KR1020027002405A KR20027002405A KR20020043565A KR 20020043565 A KR20020043565 A KR 20020043565A KR 1020027002405 A KR1020027002405 A KR 1020027002405A KR 20027002405 A KR20027002405 A KR 20027002405A KR 20020043565 A KR20020043565 A KR 20020043565A
- Authority
- KR
- South Korea
- Prior art keywords
- methoxy
- omeprazole
- isomers
- standard
- composition
- 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- Withdrawn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
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical class N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 title claims description 89
- 238000001069 Raman spectroscopy Methods 0.000 title abstract description 18
- 238000005259 measurement Methods 0.000 title abstract description 14
- 238000005079 FT-Raman Methods 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 11
- 229960000381 omeprazole Drugs 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- -1 omeprazole compound Chemical class 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 3
- 210000004211 gastric acid Anatomy 0.000 claims description 3
- 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 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 22
- 239000003814 drug Substances 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 12
- 229940079593 drug Drugs 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 8
- 229940089505 prilosec Drugs 0.000 description 8
- 239000002775 capsule Substances 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 238000001237 Raman spectrum Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000008365 aqueous carrier Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HMNBFIPHGLRDFA-BWSJPXOBSA-N (2S,3S,4R,5R)-1-methoxyhexane-1,2,3,4,5,6-hexol Chemical compound COC(O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO HMNBFIPHGLRDFA-BWSJPXOBSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009149 molecular binding Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/65—Raman scattering
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Pathology (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15087899P | 1999-08-26 | 1999-08-26 | |
| US60/150,878 | 1999-08-26 | ||
| PCT/US2000/023368 WO2001013919A1 (en) | 1999-08-26 | 2000-08-23 | Ft-raman spectroscopic measurement of omeprazole isomer ratio in a composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020043565A true KR20020043565A (ko) | 2002-06-10 |
Family
ID=22536394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027002405A Withdrawn KR20020043565A (ko) | 1999-08-26 | 2000-08-23 | 조성물에서의 오메프라졸 이성질체 비율의ｆｔ－ｒａｍａｎ 분광학적 측정 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20060014799A1 (https=) |
| EP (1) | EP1206263A1 (https=) |
| JP (1) | JP2003507721A (https=) |
| KR (1) | KR20020043565A (https=) |
| CN (2) | CN1379670A (https=) |
| AU (1) | AU6937700A (https=) |
| CA (1) | CA2382838A1 (https=) |
| MX (1) | MXPA02002068A (https=) |
| WO (1) | WO2001013919A1 (https=) |
| ZA (2) | ZA200201519B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101038818B1 (ko) * | 2003-05-19 | 2011-06-03 | 바이엘 머티리얼사이언스 아게 | 이소시아네이트 제조 공정에서 이성질체 조성을 측정하는방법 및 장치 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| CA2443605A1 (en) * | 2001-04-20 | 2002-10-31 | Linda Whittall | Process for purifying 6-methoxy omeprazole |
| US7855082B1 (en) | 2001-10-31 | 2010-12-21 | Astrazeneca Ab | Raman spectroscopic method for determining the ratio of 5-methoxy and 6-methoxy isomers of omeprazole |
| FR2937418B1 (fr) * | 2008-10-17 | 2010-12-31 | France Etat Ponts Chaussees | Procede de determination de la phase solide/liquide. |
| MX2013003038A (es) * | 2010-09-17 | 2013-05-01 | Abbvie Inc | Espectroscopia raman para operaciones de bioprocesos. |
| CN103833731B (zh) * | 2011-12-01 | 2016-03-23 | 四川大学 | 手性亚砜类化合物及其盐的制备新方法和晶型 |
| CN103006610B (zh) * | 2013-01-04 | 2014-10-22 | 青岛大学 | 一种埃索美拉唑钠肠溶片剂及其制备方法 |
| CN103408532A (zh) * | 2013-08-02 | 2013-11-27 | 常州大学 | 一种质子泵抑制剂的制备方法 |
| US9599565B1 (en) * | 2013-10-02 | 2017-03-21 | Ondax, Inc. | Identification and analysis of materials and molecular structures |
| US9587983B1 (en) | 2015-09-21 | 2017-03-07 | Ondax, Inc. | Thermally compensated optical probe |
| EP3472582A4 (en) * | 2016-06-16 | 2020-03-18 | Valisure LLC | SPECTROSCOPIC ANALYSIS METHODS AND SYSTEMS |
| CN113092445A (zh) * | 2021-04-14 | 2021-07-09 | 中朗正健(苏州)生物技术有限公司 | 一种对减肥类保健食品中违法添加奥美拉唑的检测方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| US5638172A (en) * | 1994-05-27 | 1997-06-10 | Eastman Chemical Company | On-line quantitative analysis of chemical compositions by raman spectrometry |
| US6040906A (en) * | 1996-07-11 | 2000-03-21 | Harhay; Gregory P. | Resonance raman spectroscopy for identifying and quantitating biomatter, organic, and inorganic analytes |
| US5850623A (en) * | 1997-03-14 | 1998-12-15 | Eastman Chemical Company | Method for standardizing raman spectrometers to obtain stable and transferable calibrations |
-
2000
- 2000-08-23 CN CN00814398A patent/CN1379670A/zh active Pending
- 2000-08-23 MX MXPA02002068A patent/MXPA02002068A/es unknown
- 2000-08-23 AU AU69377/00A patent/AU6937700A/en not_active Abandoned
- 2000-08-23 CA CA002382838A patent/CA2382838A1/en not_active Abandoned
- 2000-08-23 KR KR1020027002405A patent/KR20020043565A/ko not_active Withdrawn
- 2000-08-23 WO PCT/US2000/023368 patent/WO2001013919A1/en not_active Ceased
- 2000-08-23 JP JP2001518056A patent/JP2003507721A/ja active Pending
- 2000-08-23 EP EP00957808A patent/EP1206263A1/en not_active Withdrawn
- 2000-08-25 CN CNA2006101016924A patent/CN1880312A/zh active Pending
-
2002
- 2002-02-22 ZA ZA200201519A patent/ZA200201519B/xx unknown
- 2002-02-22 ZA ZA200201521A patent/ZA200201521B/xx unknown
-
2005
- 2005-08-22 US US11/208,971 patent/US20060014799A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101038818B1 (ko) * | 2003-05-19 | 2011-06-03 | 바이엘 머티리얼사이언스 아게 | 이소시아네이트 제조 공정에서 이성질체 조성을 측정하는방법 및 장치 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200201521B (en) | 2003-05-22 |
| JP2003507721A (ja) | 2003-02-25 |
| CN1379670A (zh) | 2002-11-13 |
| EP1206263A1 (en) | 2002-05-22 |
| US20060014799A1 (en) | 2006-01-19 |
| WO2001013919A1 (en) | 2001-03-01 |
| MXPA02002068A (es) | 2003-08-20 |
| CA2382838A1 (en) | 2001-03-01 |
| AU6937700A (en) | 2001-03-19 |
| CN1880312A (zh) | 2006-12-20 |
| ZA200201519B (en) | 2003-05-22 |
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